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361442-00-4

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  • High quality (Alpha S)-Alpha - [[ (1,1-Dimethylethyoxy)Carbonyl]Amino]-Alpha-(3-Hydroxyadamantan-1-Yl)Acetic Acid supplier in China

    Cas No: 361442-00-4

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361442-00-4 Usage

Uses

Boc-3-hydroxy-1-adamantyl-D-glycine is used in the preparation of a Saxagliptin intermediate.

Check Digit Verification of cas no

The CAS Registry Mumber 361442-00-4 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 3,6,1,4,4 and 2 respectively; the second part has 2 digits, 0 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 361442-00:
(8*3)+(7*6)+(6*1)+(5*4)+(4*4)+(3*2)+(2*0)+(1*0)=114
114 % 10 = 4
So 361442-00-4 is a valid CAS Registry Number.

361442-00-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name (2S)-2-((tert-Butoxycarbonyl)amino)-2-(3-hydroxyadamantan-1-yl)acetic acid

1.2 Other means of identification

Product number -
Other names Boc-3-Hydroxy-1-adamantyl-D-glycine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:361442-00-4 SDS

361442-00-4Synthetic route

N-tert-butoxycarbonyl-2-(3-hydroxy-1-adamantyl)-D-glycine ethyl ester

N-tert-butoxycarbonyl-2-(3-hydroxy-1-adamantyl)-D-glycine ethyl ester

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
With water; sodium hydroxide In ethanol at 18 - 65℃; for 2h;98.1%
(αS)-α-amino-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

(αS)-α-amino-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
With potassium carbonate In tetrahydrofuran at 20℃; for 12h;98%
With potassium phosphate In tetrahydrofuran; sodium hydroxide at 20℃; for 2h;88%
Stage #1: (αS)-α-amino-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid; di-tert-butyl dicarbonate With sodium hydroxide for 4h; pH=10;
Stage #2: With sulfuric acid In Isopropyl acetate; water for 0.0833333 - 0.166667h; pH=2.0 - 8;
88%
N-tert-butoxycarbonyl-3-hydroxy-1-adamantaneglycine

N-tert-butoxycarbonyl-3-hydroxy-1-adamantaneglycine

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
With (1R,2S)-2-Amino-1,2-diphenylethanol In ethyl acetate at 20℃; for 2h; Reflux; Resolution of racemate;56%
Multi-step reaction with 2 steps
1: ethyl acetate / 17.42 h / 20 - 70 °C / Resolution of racemate
2: hydrogenchloride / ethyl acetate; water / pH 3
View Scheme
Multi-step reaction with 2 steps
1: ethanol / 0.08 h / Resolution of racemate; Reflux
2: hydrogenchloride / water; ethyl acetate / pH 2
View Scheme
(alpha S)-alpha-[[(1,1-dimethylethoxy)carbonyl]amino]tricyclo[3.3.1.13,7]decane-1-acetic acid
361441-97-6

(alpha S)-alpha-[[(1,1-dimethylethoxy)carbonyl]amino]tricyclo[3.3.1.13,7]decane-1-acetic acid

A

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

B

(S)-2-((tert-butoxycarbonyl)amino)-2-(3,5-dihydroxyadamantan-1-yl)acetic acid
681282-72-4

(S)-2-((tert-butoxycarbonyl)amino)-2-(3,5-dihydroxyadamantan-1-yl)acetic acid

Conditions
ConditionsYield
With potassium hydroxide; potassium permanganate at 60 - 90℃; for 1.5h;A 51%
B 17%
With potassium hydroxide; potassium permanganate In water at 60 - 90℃; for 1.5h;A 51%
B 17%
(alpha S)-alpha-[[(1,1-dimethylethoxy)carbonyl]amino]tricyclo[3.3.1.13,7]decane-1-acetic acid
361441-97-6

(alpha S)-alpha-[[(1,1-dimethylethoxy)carbonyl]amino]tricyclo[3.3.1.13,7]decane-1-acetic acid

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
With potassium permanganate; water; potassium hydroxide at 60 - 90℃; for 1.5h;51%
With potassium permanganate; potassium hydroxide at 90℃;49%
With potassium permanganate; tetrabutylammomium bromide; potassium hydroxide In water at 20 - 25℃;18.6 g
(S)-2-(adamantan-1-yl)-2-(((R)-2-hydroxy-1-phenylethyl)amino)acetonitrile
361441-95-4

(S)-2-(adamantan-1-yl)-2-(((R)-2-hydroxy-1-phenylethyl)amino)acetonitrile

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 78 percent / aq. HCl; AcOH / 18 h / 80 °C
2: H2; AcOH / Pd(OH)2/C / methanol / 18 h / 2585.74 Torr
3: 4.07 g / K2CO3 / dimethylformamide / 19 h
4: 51 percent / KMnO4; aq. KOH / 1.5 h / 60 - 90 °C
View Scheme
Multi-step reaction with 4 steps
1: hydrogenchloride; water / acetic acid / 80 °C
2: hydrogen; palladium 10% on activated carbon / acetic acid
3: triethylamine / methanol
4: potassium permanganate; potassium hydroxide / 90 °C
View Scheme
Multi-step reaction with 4 steps
1.1: hydrogenchloride; acetic acid; water / 20 - 95 °C
2.1: acetic acid; hydrogen; 10% palladium hydroxide on charcoal / methanol / 20 °C
3.1: sodium hydroxide / water / 0.25 h / 0 - 5 °C
3.2: 0 - 5 °C
4.1: potassium permanganate; potassium hydroxide; tetrabutylammomium bromide / water / 20 - 25 °C
View Scheme
Multi-step reaction with 4 steps
1: hydrogenchloride; water / acetic acid / 18 h / 80 °C
2: hydrogen; 20% palladium hydroxide-activated charcoal / methanol; acetic acid / 18 h / 2585.81 Torr
3: potassium carbonate / N,N-dimethyl-formamide / 19 h / 20 °C / Inert atmosphere
4: water; potassium permanganate; potassium hydroxide / 1.5 h / 60 - 90 °C
View Scheme
(R)-N-((S)-(adamantan-1-yl)(carboxy)methyl)-2-hydroxy-1-phenylethan-1-ammonium chloride

(R)-N-((S)-(adamantan-1-yl)(carboxy)methyl)-2-hydroxy-1-phenylethan-1-ammonium chloride

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: H2; AcOH / Pd(OH)2/C / methanol / 18 h / 2585.74 Torr
2: 4.07 g / K2CO3 / dimethylformamide / 19 h
3: 51 percent / KMnO4; aq. KOH / 1.5 h / 60 - 90 °C
View Scheme
Multi-step reaction with 3 steps
1: hydrogen; palladium 10% on activated carbon / acetic acid
2: triethylamine / methanol
3: potassium permanganate; potassium hydroxide / 90 °C
View Scheme
Multi-step reaction with 3 steps
1.1: acetic acid; hydrogen; 10% palladium hydroxide on charcoal / methanol / 20 °C
2.1: sodium hydroxide / water / 0.25 h / 0 - 5 °C
2.2: 0 - 5 °C
3.1: potassium permanganate; potassium hydroxide; tetrabutylammomium bromide / water / 20 - 25 °C
View Scheme
Multi-step reaction with 3 steps
1: hydrogen; 20% palladium hydroxide-activated charcoal / methanol; acetic acid / 18 h / 2585.81 Torr
2: potassium carbonate / N,N-dimethyl-formamide / 19 h / 20 °C / Inert atmosphere
3: water; potassium permanganate; potassium hydroxide / 1.5 h / 60 - 90 °C
View Scheme
1-adamantanemethanol
770-71-8

1-adamantanemethanol

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 98 percent / oxalyl chloride; DMSO; Et3N / CH2Cl2 / 1 h / -78 °C
2: 65 percent / NaHSO3 / H2O; methanol / 16 h / Heating
3: 78 percent / aq. HCl; AcOH / 18 h / 80 °C
4: H2; AcOH / Pd(OH)2/C / methanol / 18 h / 2585.74 Torr
5: 4.07 g / K2CO3 / dimethylformamide / 19 h
6: 51 percent / KMnO4; aq. KOH / 1.5 h / 60 - 90 °C
View Scheme
Multi-step reaction with 6 steps
1.1: potassium bromide; sodium hydrogencarbonate / dichloromethane / 0.25 h / 0 - 5 °C
1.2: 0 - 5 °C
2.1: sodium hydrogensulfite / methanol; water / 0 - 55 °C
3.1: hydrogenchloride; acetic acid; water / 20 - 95 °C
4.1: acetic acid; hydrogen; 10% palladium hydroxide on charcoal / methanol / 20 °C
5.1: sodium hydroxide / water / 0.25 h / 0 - 5 °C
5.2: 0 - 5 °C
6.1: potassium permanganate; potassium hydroxide; tetrabutylammomium bromide / water / 20 - 25 °C
View Scheme
Multi-step reaction with 6 steps
1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere
1.2: 0.5 h / -78 °C / Inert atmosphere
2.1: sodium hydrogensulfite / methanol; water / 18 h / 0 - 20 °C / Reflux
3.1: hydrogenchloride; water / acetic acid / 18 h / 80 °C
4.1: hydrogen; 20% palladium hydroxide-activated charcoal / methanol; acetic acid / 18 h / 2585.81 Torr
5.1: potassium carbonate / N,N-dimethyl-formamide / 19 h / 20 °C / Inert atmosphere
6.1: water; potassium permanganate; potassium hydroxide / 1.5 h / 60 - 90 °C
View Scheme
Multi-step reaction with 7 steps
1.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hypochlorite; sodium bromide / dichloromethane; water / 12 h / 5 - 30 °C
2.1: sodium hydrogen sulfate / water; methanol / 5 - 77 °C
3.1: sulfuric acid / 45 - 50 °C
3.2: 2 h / 20 - 35 °C
4.1: 10 wt% Pd(OH)2 on carbon; acetic acid; hydrogen / methanol / 760.05 Torr
5.1: sulfuric acid / 110 - 112 °C
6.1: sulfuric acid; nitric acid / 10 - 25 °C
7.1: sodium hydroxide / 5 h / 25 - 30 °C
View Scheme
1-Adamantanecarboxylic acid
828-51-3

1-Adamantanecarboxylic acid

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 100 percent / diethyl ether; hexane; methanol / 3 h / 20 °C
2: 96 percent / LiAlH4 / tetrahydrofuran / 1.5 h / 0 - 20 °C
3: 98 percent / oxalyl chloride; DMSO; Et3N / CH2Cl2 / 1 h / -78 °C
4: 65 percent / NaHSO3 / H2O; methanol / 16 h / Heating
5: 78 percent / aq. HCl; AcOH / 18 h / 80 °C
6: H2; AcOH / Pd(OH)2/C / methanol / 18 h / 2585.74 Torr
7: 4.07 g / K2CO3 / dimethylformamide / 19 h
8: 51 percent / KMnO4; aq. KOH / 1.5 h / 60 - 90 °C
View Scheme
Multi-step reaction with 8 steps
1.1: thionyl chloride / 3 h / 20 °C
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere
3.1: potassium bromide; sodium hydrogencarbonate / dichloromethane / 0.25 h / 0 - 5 °C
3.2: 0 - 5 °C
4.1: sodium hydrogensulfite / methanol; water / 0 - 55 °C
5.1: hydrogenchloride; acetic acid; water / 20 - 95 °C
6.1: acetic acid; hydrogen; 10% palladium hydroxide on charcoal / methanol / 20 °C
7.1: sodium hydroxide / water / 0.25 h / 0 - 5 °C
7.2: 0 - 5 °C
8.1: potassium permanganate; potassium hydroxide; tetrabutylammomium bromide / water / 20 - 25 °C
View Scheme
Multi-step reaction with 8 steps
1.1: thionyl chloride / 4 h / Reflux
2.1: sodium / Petroleum ether / 20 °C
2.2: 20 °C
2.3: 6 h / Reflux
3.1: sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; potassium permanganate / water; tert-butyl alcohol / 3 h / 40 - 45 °C
4.1: sodium hydroxide; hydroxylamine hydrochloride / water / 2 h
5.1: sodium hydroxide; nickel aluminum / ethanol / 8 h / 50 °C
6.1: hydrogenchloride / water; tetrahydrofuran / 20 °C / pH 10
7.1: potassium permanganate; potassium hydroxide / 2 h / 90 °C
8.1: (1R,2S)-2-Amino-1,2-diphenylethanol / ethyl acetate / 2 h / 20 °C / Reflux; Resolution of racemate
View Scheme
1-Adamantanecarbaldehyde
2094-74-8

1-Adamantanecarbaldehyde

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 65 percent / NaHSO3 / H2O; methanol / 16 h / Heating
2: 78 percent / aq. HCl; AcOH / 18 h / 80 °C
3: H2; AcOH / Pd(OH)2/C / methanol / 18 h / 2585.74 Torr
4: 4.07 g / K2CO3 / dimethylformamide / 19 h
5: 51 percent / KMnO4; aq. KOH / 1.5 h / 60 - 90 °C
View Scheme
Multi-step reaction with 5 steps
1: sodium hydrogensulfite / 0 - 60 °C
2: hydrogenchloride; water / acetic acid / 80 °C
3: hydrogen; palladium 10% on activated carbon / acetic acid
4: triethylamine / methanol
5: potassium permanganate; potassium hydroxide / 90 °C
View Scheme
Multi-step reaction with 5 steps
1.1: sodium hydrogensulfite / methanol; water / 0 - 55 °C
2.1: hydrogenchloride; acetic acid; water / 20 - 95 °C
3.1: acetic acid; hydrogen; 10% palladium hydroxide on charcoal / methanol / 20 °C
4.1: sodium hydroxide / water / 0.25 h / 0 - 5 °C
4.2: 0 - 5 °C
5.1: potassium permanganate; potassium hydroxide; tetrabutylammomium bromide / water / 20 - 25 °C
View Scheme
Multi-step reaction with 5 steps
1: sodium hydrogensulfite / methanol; water / 18 h / 0 - 20 °C / Reflux
2: hydrogenchloride; water / acetic acid / 18 h / 80 °C
3: hydrogen; 20% palladium hydroxide-activated charcoal / methanol; acetic acid / 18 h / 2585.81 Torr
4: potassium carbonate / N,N-dimethyl-formamide / 19 h / 20 °C / Inert atmosphere
5: water; potassium permanganate; potassium hydroxide / 1.5 h / 60 - 90 °C
View Scheme
Multi-step reaction with 6 steps
1.1: sodium hydrogen sulfate / water; methanol / 5 - 77 °C
2.1: sulfuric acid / 45 - 50 °C
2.2: 2 h / 20 - 35 °C
3.1: 10 wt% Pd(OH)2 on carbon; acetic acid; hydrogen / methanol / 760.05 Torr
4.1: sulfuric acid / 110 - 112 °C
5.1: sulfuric acid; nitric acid / 10 - 25 °C
6.1: sodium hydroxide / 5 h / 25 - 30 °C
View Scheme
methyl adamantane-1-carboxylate
711-01-3

methyl adamantane-1-carboxylate

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 96 percent / LiAlH4 / tetrahydrofuran / 1.5 h / 0 - 20 °C
2: 98 percent / oxalyl chloride; DMSO; Et3N / CH2Cl2 / 1 h / -78 °C
3: 65 percent / NaHSO3 / H2O; methanol / 16 h / Heating
4: 78 percent / aq. HCl; AcOH / 18 h / 80 °C
5: H2; AcOH / Pd(OH)2/C / methanol / 18 h / 2585.74 Torr
6: 4.07 g / K2CO3 / dimethylformamide / 19 h
7: 51 percent / KMnO4; aq. KOH / 1.5 h / 60 - 90 °C
View Scheme
Multi-step reaction with 7 steps
1.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere
2.1: potassium bromide; sodium hydrogencarbonate / dichloromethane / 0.25 h / 0 - 5 °C
2.2: 0 - 5 °C
3.1: sodium hydrogensulfite / methanol; water / 0 - 55 °C
4.1: hydrogenchloride; acetic acid; water / 20 - 95 °C
5.1: acetic acid; hydrogen; 10% palladium hydroxide on charcoal / methanol / 20 °C
6.1: sodium hydroxide / water / 0.25 h / 0 - 5 °C
6.2: 0 - 5 °C
7.1: potassium permanganate; potassium hydroxide; tetrabutylammomium bromide / water / 20 - 25 °C
View Scheme
Multi-step reaction with 7 steps
1.1: lithium aluminium tetrahydride / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere
2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere
2.2: 0.5 h / -78 °C / Inert atmosphere
3.1: sodium hydrogensulfite / methanol; water / 18 h / 0 - 20 °C / Reflux
4.1: hydrogenchloride; water / acetic acid / 18 h / 80 °C
5.1: hydrogen; 20% palladium hydroxide-activated charcoal / methanol; acetic acid / 18 h / 2585.81 Torr
6.1: potassium carbonate / N,N-dimethyl-formamide / 19 h / 20 °C / Inert atmosphere
7.1: water; potassium permanganate; potassium hydroxide / 1.5 h / 60 - 90 °C
View Scheme
(S)-(+)-β-amino-1-adamantaneacetic acid
95853-35-3

(S)-(+)-β-amino-1-adamantaneacetic acid

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 4.07 g / K2CO3 / dimethylformamide / 19 h
2: 51 percent / KMnO4; aq. KOH / 1.5 h / 60 - 90 °C
View Scheme
Multi-step reaction with 2 steps
1: sulfuric acid; nitric acid / 10 - 25 °C
2: sodium hydroxide / 5 h / 25 - 30 °C
View Scheme
(αS)-α-[(1,1-dimethylethoxy)carbonyl]amino-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

(αS)-α-[(1,1-dimethylethoxy)carbonyl]amino-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
With hydrogenchloride In water; ethyl acetate pH=3;
N-tert-butoxycarbonyl-2-(3-hydroxy-1-adamantyl)-D-glycine
1334321-39-9

N-tert-butoxycarbonyl-2-(3-hydroxy-1-adamantyl)-D-glycine

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: N-ethyl-N,N-diisopropylamine; isobutyl chloroformate / tetrahydrofuran / 1.5 h / -8 °C
1.2: 18 h / -8 - 25 °C
2.1: ethyl acetate / 17.42 h / 20 - 70 °C / Resolution of racemate
3.1: hydrogenchloride / ethyl acetate; water / pH 3
View Scheme
Multi-step reaction with 3 steps
1.1: dicyclohexyl-carbodiimide / dimethyl sulfoxide / 5 h / 20 °C
1.2: 53 h / 20 - 50 °C
1.3: 2 h
2.1: ethanol / 0.08 h / Resolution of racemate; Reflux
3.1: hydrogenchloride / water; ethyl acetate / pH 2
View Scheme
(S)-(+)-(adamant-1-yl)aminoacetic acid hydrochloride
102502-64-7

(S)-(+)-(adamant-1-yl)aminoacetic acid hydrochloride

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / methanol
2: potassium permanganate; potassium hydroxide / 90 °C
View Scheme
Multi-step reaction with 2 steps
1: potassium carbonate / N,N-dimethyl-formamide / 19 h / 20 °C / Inert atmosphere
2: water; potassium permanganate; potassium hydroxide / 1.5 h / 60 - 90 °C
View Scheme
2-(adamantan-1-yl)-2-aminoacetic acid
59768-71-7, 60256-21-5, 95853-35-3, 100926-41-8

2-(adamantan-1-yl)-2-aminoacetic acid

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrogenchloride / water; tetrahydrofuran / 20 °C / pH 10
2: potassium permanganate; potassium hydroxide / 2 h / 90 °C
3: (1R,2S)-2-Amino-1,2-diphenylethanol / ethyl acetate / 2 h / 20 °C / Reflux; Resolution of racemate
View Scheme
1-acetyladamantane
1660-04-4

1-acetyladamantane

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; potassium permanganate / water; tert-butyl alcohol / 3 h / 40 - 45 °C
2: sodium hydroxide; hydroxylamine hydrochloride / water / 2 h
3: sodium hydroxide; nickel aluminum / ethanol / 8 h / 50 °C
4: hydrogenchloride / water; tetrahydrofuran / 20 °C / pH 10
5: potassium permanganate; potassium hydroxide / 2 h / 90 °C
6: (1R,2S)-2-Amino-1,2-diphenylethanol / ethyl acetate / 2 h / 20 °C / Reflux; Resolution of racemate
View Scheme
oxo-tricyclo[3.3.1.13,7]decan-1-yl-acetic acid
16091-98-8

oxo-tricyclo[3.3.1.13,7]decan-1-yl-acetic acid

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: sodium hydroxide; hydroxylamine hydrochloride / water / 2 h
2: sodium hydroxide; nickel aluminum / ethanol / 8 h / 50 °C
3: hydrogenchloride / water; tetrahydrofuran / 20 °C / pH 10
4: potassium permanganate; potassium hydroxide / 2 h / 90 °C
5: (1R,2S)-2-Amino-1,2-diphenylethanol / ethyl acetate / 2 h / 20 °C / Reflux; Resolution of racemate
View Scheme
1-adamantyl-2-hydroxyiminoacetic acid
16091-97-7

1-adamantyl-2-hydroxyiminoacetic acid

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: sodium hydroxide; nickel aluminum / ethanol / 8 h / 50 °C
2: hydrogenchloride / water; tetrahydrofuran / 20 °C / pH 10
3: potassium permanganate; potassium hydroxide / 2 h / 90 °C
4: (1R,2S)-2-Amino-1,2-diphenylethanol / ethyl acetate / 2 h / 20 °C / Reflux; Resolution of racemate
View Scheme
1-Adamantanecarbonyl chloride
2094-72-6

1-Adamantanecarbonyl chloride

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: sodium / Petroleum ether / 20 °C
1.2: 20 °C
1.3: 6 h / Reflux
2.1: sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; potassium permanganate / water; tert-butyl alcohol / 3 h / 40 - 45 °C
3.1: sodium hydroxide; hydroxylamine hydrochloride / water / 2 h
4.1: sodium hydroxide; nickel aluminum / ethanol / 8 h / 50 °C
5.1: hydrogenchloride / water; tetrahydrofuran / 20 °C / pH 10
6.1: potassium permanganate; potassium hydroxide / 2 h / 90 °C
7.1: (1R,2S)-2-Amino-1,2-diphenylethanol / ethyl acetate / 2 h / 20 °C / Reflux; Resolution of racemate
View Scheme
3-hydroxytricyclo[3.3.1.13'7]decane-1-carbaldehyde

3-hydroxytricyclo[3.3.1.13'7]decane-1-carbaldehyde

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: sodium hydrogensulfite / water / 0.17 h / 0 - 2 °C
2.1: water / 0.17 h / 0 - 2 °C
2.2: 14.5 h / -4 - 80 °C
3.1: hydrogenchloride; water / 1 h / 24 - 80 °C
3.2: 12 h / 80 - 82 °C
4.1: acetic acid; palladium(II) hydroxide; hydrogen / methanol / 5 h / 48 - 52 °C / 2625.26 - 3000.3 Torr
5.1: potassium carbonate; water / tetrahydrofuran / 0.17 h / 3 - 10 °C
5.2: 2.08 h / 3 - 26 °C
5.3: 12 h / 40 °C
View Scheme
C11H17O5S(1-)*Na(1+)

C11H17O5S(1-)*Na(1+)

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: water / 0.17 h / 0 - 2 °C
1.2: 14.5 h / -4 - 80 °C
2.1: hydrogenchloride; water / 1 h / 24 - 80 °C
2.2: 12 h / 80 - 82 °C
3.1: acetic acid; palladium(II) hydroxide; hydrogen / methanol / 5 h / 48 - 52 °C / 2625.26 - 3000.3 Torr
4.1: potassium carbonate; water / tetrahydrofuran / 0.17 h / 3 - 10 °C
4.2: 2.08 h / 3 - 26 °C
4.3: 12 h / 40 °C
View Scheme
(2S)-[((1S)-2-hydroxy-1-phenylethyl)amino]-(3-hydroxytricyclo[3.3.1.13'7]dec-1-yl)ethanenitrile

(2S)-[((1S)-2-hydroxy-1-phenylethyl)amino]-(3-hydroxytricyclo[3.3.1.13'7]dec-1-yl)ethanenitrile

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: hydrogenchloride; water / 1 h / 24 - 80 °C
1.2: 12 h / 80 - 82 °C
2.1: acetic acid; palladium(II) hydroxide; hydrogen / methanol / 5 h / 48 - 52 °C / 2625.26 - 3000.3 Torr
3.1: potassium carbonate; water / tetrahydrofuran / 0.17 h / 3 - 10 °C
3.2: 2.08 h / 3 - 26 °C
3.3: 12 h / 40 °C
View Scheme
(2S)-[3-chlorotricyclo[3.3.1.13'7]dec-1-yl]-[((1S)-2-hydroxy-1-phenylethyl)amino]ethanoic acid hydrochloride

(2S)-[3-chlorotricyclo[3.3.1.13'7]dec-1-yl]-[((1S)-2-hydroxy-1-phenylethyl)amino]ethanoic acid hydrochloride

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: acetic acid; palladium(II) hydroxide; hydrogen / methanol / 5 h / 48 - 52 °C / 2625.26 - 3000.3 Torr
2.1: potassium carbonate; water / tetrahydrofuran / 0.17 h / 3 - 10 °C
2.2: 2.08 h / 3 - 26 °C
2.3: 12 h / 40 °C
View Scheme
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

(2S)-amino[3-chlorotricyclo[3.3.1.13'7]dec-1-yl]ethanoic acid hydrochloride

(2S)-amino[3-chlorotricyclo[3.3.1.13'7]dec-1-yl]ethanoic acid hydrochloride

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
Stage #1: (2S)-amino[3-chlorotricyclo[3.3.1.13'7]dec-1-yl]ethanoic acid hydrochloride With water; potassium carbonate In tetrahydrofuran at 3 - 10℃; for 0.166667h;
Stage #2: di-tert-butyl dicarbonate In tetrahydrofuran at 3 - 26℃; for 2.08333h;
Stage #3: With water at 40℃; for 12h;
1.16 g
3-hydroxyadamantane-1-carboxylic acid
42711-75-1

3-hydroxyadamantane-1-carboxylic acid

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: sodium tetrahydroborate / tetrahydrofuran / 2.5 h / 0 - 31 °C
1.2: 14.5 h / 0 - 30 °C
1.3: 1 h / 0 - 10 °C
2.1: potassium bromide; sodium hydrogencarbonate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hypochlorite / dichloromethane; water / 0 - 5 °C
3.1: sodium hydrogensulfite / water / 0.17 h / 0 - 2 °C
4.1: water / 0.17 h / 0 - 2 °C
4.2: 14.5 h / -4 - 80 °C
5.1: hydrogenchloride; water / 1 h / 24 - 80 °C
5.2: 12 h / 80 - 82 °C
6.1: acetic acid; palladium(II) hydroxide; hydrogen / methanol / 5 h / 48 - 52 °C / 2625.26 - 3000.3 Torr
7.1: potassium carbonate; water / tetrahydrofuran / 0.17 h / 3 - 10 °C
7.2: 2.08 h / 3 - 26 °C
7.3: 12 h / 40 °C
View Scheme
1-hydroxy-3-hydroxymethyladamantane
38584-37-1

1-hydroxy-3-hydroxymethyladamantane

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: potassium bromide; sodium hydrogencarbonate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hypochlorite / dichloromethane; water / 0 - 5 °C
2.1: sodium hydrogensulfite / water / 0.17 h / 0 - 2 °C
3.1: water / 0.17 h / 0 - 2 °C
3.2: 14.5 h / -4 - 80 °C
4.1: hydrogenchloride; water / 1 h / 24 - 80 °C
4.2: 12 h / 80 - 82 °C
5.1: acetic acid; palladium(II) hydroxide; hydrogen / methanol / 5 h / 48 - 52 °C / 2625.26 - 3000.3 Torr
6.1: potassium carbonate; water / tetrahydrofuran / 0.17 h / 3 - 10 °C
6.2: 2.08 h / 3 - 26 °C
6.3: 12 h / 40 °C
View Scheme
1-acetyl-3-chloroadamantane
143467-20-3

1-acetyl-3-chloroadamantane

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: potassium hydroxide / water / 6 h / Reflux
2: potassium hydroxide; potassium permanganate / water; tert-butyl alcohol / 4.5 h / 35 - 45 °C
3: sodium hydroxide; hydroxylamine hydrochloride / water / 2 h / 0 - 5 °C / pH 7
4: sodium hydroxide; nickel-aluminum alloy / water / 50 °C
5: hydrogenchloride / water; tetrahydrofuran / 12 h / 20 °C / pH 10
6: ethanol / 0.08 h / Resolution of racemate; Reflux
7: hydrogenchloride / water; ethyl acetate / pH 2
View Scheme
C12H18NO3(1-)*Na(1+)

C12H18NO3(1-)*Na(1+)

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrogenchloride / water; tetrahydrofuran / 12 h / 20 °C / pH 10
2: ethanol / 0.08 h / Resolution of racemate; Reflux
3: hydrogenchloride / water; ethyl acetate / pH 2
View Scheme
C17H27NO5*C20H24N2O2

C17H27NO5*C20H24N2O2

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
With hydrogenchloride In water; ethyl acetate pH=2;0.96 g
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-3-carboxamide methane sulphonic acid
709031-45-8

(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-3-carboxamide methane sulphonic acid

tert-butyl [(1S)-2-[(1S,3S,5S)-3-carbamoyl-2-azabicyclo[3.1.0]hex-2-yl]-1-(3-hydroxytricyclo[3.3.1.13'7]dec-1-yl)-2-oxoethyl]carbamate
361442-01-5

tert-butyl [(1S)-2-[(1S,3S,5S)-3-carbamoyl-2-azabicyclo[3.1.0]hex-2-yl]-1-(3-hydroxytricyclo[3.3.1.13'7]dec-1-yl)-2-oxoethyl]carbamate

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In ethyl acetate; acetonitrile Solvent; Large scale;98.1%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In ethyl acetate; acetonitrile for 3h;46%
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

cis-2-azabicyclo[3.1.0]hexane hydrochloride
841302-41-8

cis-2-azabicyclo[3.1.0]hexane hydrochloride

(2S,3R)-1-[(2S)-N-Boc-2-(3-hydroxyadamant-1-yl)glycin]-2,3-methanopyrrolidine
841302-42-9

(2S,3R)-1-[(2S)-N-Boc-2-(3-hydroxyadamant-1-yl)glycin]-2,3-methanopyrrolidine

Conditions
ConditionsYield
With 4-methyl-morpholine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate In dichloromethane at 20℃; for 20h;97.5%
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

bis(pentafluorophenyl)carbonate
59483-84-0

bis(pentafluorophenyl)carbonate

pentafluorophenyl (2S)-2-((t-butoxycarbonyl)amino)-2-(3-hydroxyadamantan-1-yl)acetate

pentafluorophenyl (2S)-2-((t-butoxycarbonyl)amino)-2-(3-hydroxyadamantan-1-yl)acetate

Conditions
ConditionsYield
Stage #1: (αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid With triethylamine In ethyl acetate at 25℃; for 0.666667h;
Stage #2: bis(pentafluorophenyl)carbonate In ethyl acetate at 25℃; for 2h;
93.1%
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

D-cis-4,5-methanoprolineamide methanesulfonic acid salt
1312338-82-1

D-cis-4,5-methanoprolineamide methanesulfonic acid salt

(S)-N-Boc-3-hydroxyadamantylglycine-D-cis-4,5-methanoprolinamide
1564266-87-0

(S)-N-Boc-3-hydroxyadamantylglycine-D-cis-4,5-methanoprolinamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In ethyl acetate; acetonitrile for 3h;93%
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

2,2'-dipyridyl carbonate
1659-31-0

2,2'-dipyridyl carbonate

2-pyridyl (2S)-2-((t-butoxycarbonyl)amino)-2-(3-hydroxyadamantan-1-yl)acetate

2-pyridyl (2S)-2-((t-butoxycarbonyl)amino)-2-(3-hydroxyadamantan-1-yl)acetate

Conditions
ConditionsYield
Stage #1: (αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid With triethylamine In ethyl acetate at 25℃; for 0.666667h;
Stage #2: 2,2'-dipyridyl carbonate In ethyl acetate at 25℃; for 3h;
92.2%
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

(1S)-α-amino-3-hydroxyadamantane-acetic acid hydrochloride
865999-64-0

(1S)-α-amino-3-hydroxyadamantane-acetic acid hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In dichloromethane; isopropyl alcohol at 10 - 35℃; for 8h;90%
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

bis-(p-nitrophenyl) carbonate
5070-13-3

bis-(p-nitrophenyl) carbonate

4-nitrophenyl (2S)-2-((t-butoxycarbonyl)amino)-2-(3-hydroxyadamantan-1-yl)acetate

4-nitrophenyl (2S)-2-((t-butoxycarbonyl)amino)-2-(3-hydroxyadamantan-1-yl)acetate

Conditions
ConditionsYield
Stage #1: (αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid With dmap; triethylamine In N,N-dimethyl-formamide at 25℃; for 0.666667h;
Stage #2: bis-(p-nitrophenyl) carbonate In N,N-dimethyl-formamide at 70℃; for 5h; Solvent;
90%
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

1-hydroxy-pyrrolidine-2,5-dione
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

(S)-N-boc-(3-hydroxyadamantan-1-yl)glycine succinimide ester

(S)-N-boc-(3-hydroxyadamantan-1-yl)glycine succinimide ester

Conditions
ConditionsYield
With triethylamine In dichloromethane at 25℃; for 1h;90%
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-3-carboxamide

(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-3-carboxamide

tert-butyl [(1S)-2-[(1S,3S,5S)-3-carbamoyl-2-azabicyclo[3.1.0]hex-2-yl]-1-(3-hydroxytricyclo[3.3.1.13'7]dec-1-yl)-2-oxoethyl]carbamate
361442-01-5

tert-butyl [(1S)-2-[(1S,3S,5S)-3-carbamoyl-2-azabicyclo[3.1.0]hex-2-yl]-1-(3-hydroxytricyclo[3.3.1.13'7]dec-1-yl)-2-oxoethyl]carbamate

Conditions
ConditionsYield
Stage #1: (αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid; (1S,3S,5S)-2-azabicyclo[3.1.0]hexane-3-carboxamide With N-ethyl-N,N-diisopropylamine In ethyl acetate at 0℃; for 0.5h;
Stage #2: With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In ethyl acetate at 0 - 20℃; for 4.5h;
89.3%
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

(2S,4S,5S)-4,5-methano-L-proline carboxylamide trifluoroacetate

(2S,4S,5S)-4,5-methano-L-proline carboxylamide trifluoroacetate

tert-butyl [(1S)-2-[(1S,3S,5S)-3-carbamoyl-2-azabicyclo[3.1.0]hex-2-yl]-1-(3-hydroxytricyclo[3.3.1.13'7]dec-1-yl)-2-oxoethyl]carbamate
361442-01-5

tert-butyl [(1S)-2-[(1S,3S,5S)-3-carbamoyl-2-azabicyclo[3.1.0]hex-2-yl]-1-(3-hydroxytricyclo[3.3.1.13'7]dec-1-yl)-2-oxoethyl]carbamate

Conditions
ConditionsYield
With TEA; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃;85%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 0 - 20℃;85%
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

1,4-diaza-bicyclo[2.2.2]octane
280-57-9

1,4-diaza-bicyclo[2.2.2]octane

(<αS)-<α[[(1,1-dimethylethoxy)carbonyl]amino]-3-hydroxytricyclo[3.3.1.137] decane-1-acetic acid DABCO salt
709031-42-5

(<αS)-<α[[(1,1-dimethylethoxy)carbonyl]amino]-3-hydroxytricyclo[3.3.1.137] decane-1-acetic acid DABCO salt

Conditions
ConditionsYield
In Isopropyl acetate; water; ethyl acetate at 20℃;79%
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

L-trans-4,5-methanoprolineamide methanesulfonic acid salt
1564266-70-1

L-trans-4,5-methanoprolineamide methanesulfonic acid salt

(S)-N-Boc-3-hydroxyadamantylglycine-L-trans-4,5-methanoprolinamide

(S)-N-Boc-3-hydroxyadamantylglycine-L-trans-4,5-methanoprolinamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In ethyl acetate; acetonitrile for 3h;79%
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

D-trans-4,5-methanoprolineamide methanesulfonic acid salt
1564266-74-5

D-trans-4,5-methanoprolineamide methanesulfonic acid salt

(S)-N-Boc-3-hydroxyadamantylglycine-D-trans-4,5-methanoprolinamide
1564267-02-2

(S)-N-Boc-3-hydroxyadamantylglycine-D-trans-4,5-methanoprolinamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In ethyl acetate; acetonitrile for 3h;71%
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

(1RS,5SR)-2-azabicyclo[3.1.0]hexane hydrochloride
841302-37-2

(1RS,5SR)-2-azabicyclo[3.1.0]hexane hydrochloride

A

(2R,3S)-1-[(2S)-N-Boc-2-(3-hydroxyadamant-1-yl)glycin]-2,3-methanopyrrolidine
841302-55-4

(2R,3S)-1-[(2S)-N-Boc-2-(3-hydroxyadamant-1-yl)glycin]-2,3-methanopyrrolidine

B

(2S,3R)-1-[(2S)-N-Boc-2-(3-hydroxyadamant-1-yl)glycin]-2,3-methanopyrrolidine
841302-42-9

(2S,3R)-1-[(2S)-N-Boc-2-(3-hydroxyadamant-1-yl)glycin]-2,3-methanopyrrolidine

Conditions
ConditionsYield
With 4-methyl-morpholine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate In dichloromethane at 20℃; for 20h;A 27.4%
B 40.6%
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

(S)-2-((tert-butoxycarbonyl)amino)-2-(3,5-dihydroxyadamantan-1-yl)acetic acid
681282-72-4

(S)-2-((tert-butoxycarbonyl)amino)-2-(3,5-dihydroxyadamantan-1-yl)acetic acid

Conditions
ConditionsYield
With potassium permanganate; potassium hydroxide In water at 60 - 85℃; for 1.5h;25%
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

N-(cyanomethyl)ethylamine
24426-40-2

N-(cyanomethyl)ethylamine

[(cyanomethyl-ethyl-carbamoyl)-(3-hydroxy-adamantan-1-yl)-methyl]-carbamic acid tert-butyl ester

[(cyanomethyl-ethyl-carbamoyl)-(3-hydroxy-adamantan-1-yl)-methyl]-carbamic acid tert-butyl ester

Conditions
ConditionsYield
With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

(methylamino)acetonitrile
5616-32-0

(methylamino)acetonitrile

[(cyanomethyl-methyl-carbamoyl)-(3-hydroxy-adamantan-1-yl)-methyl]-carbamic acid tert-butyl ester

[(cyanomethyl-methyl-carbamoyl)-(3-hydroxy-adamantan-1-yl)-methyl]-carbamic acid tert-butyl ester

Conditions
ConditionsYield
With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

2-amino-N-cyanomethyl-2-(3-hydroxy-adamantan-1-yl)-N-methyl-acetamide

2-amino-N-cyanomethyl-2-(3-hydroxy-adamantan-1-yl)-N-methyl-acetamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: EDAC; HOAt; Et3N / CH2Cl2
2: TFA / CH2Cl2
View Scheme
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

2-amino-N-cyanomethyl-N-ethyl-2-(3-hydroxy-adamantan-1-yl)-acetamide

2-amino-N-cyanomethyl-N-ethyl-2-(3-hydroxy-adamantan-1-yl)-acetamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: EDAC; HOAt; Et3N / CH2Cl2
2: TFA / CH2Cl2
View Scheme
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

[(S)-2-((1S,3S,5S)-3-Cyano-2-aza-bicyclo[3.1.0]hex-2-yl)-1-(3-fluoro-adamantan-1-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester

[(S)-2-((1S,3S,5S)-3-Cyano-2-aza-bicyclo[3.1.0]hex-2-yl)-1-(3-fluoro-adamantan-1-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 85 percent / EDAC; HOBT; TEA / dimethylformamide / 20 °C
2: 94 percent / diethylaminosulfur trifluoride / CH2Cl2 / 0.25 h / -78 °C
3: 82 percent / imidazole; pyridine; POCl3 / -20 °C
View Scheme
Multi-step reaction with 3 steps
1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; triethylamine / N,N-dimethyl-formamide / 0 - 20 °C
2: diethylamino-sulfur trifluoride / dichloromethane / 0.25 h / -78 °C / Inert atmosphere
3: 1H-imidazole; pyridine; trichlorophosphate / 0.67 h / -30 °C / Inert atmosphere
View Scheme
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

3-cyano-(αS)-α-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)-β-oxo-(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-2-ethanecarbamic acid 1,1-dimethylethyl ester
709031-43-6

3-cyano-(αS)-α-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)-β-oxo-(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-2-ethanecarbamic acid 1,1-dimethylethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 85 percent / EDAC; HOBT; TEA / dimethylformamide / 20 °C
2.1: pyridine; trifluoroacetic anhydride / tetrahydrofuran / 1 h
2.2: 92 percent / aq. KOH / methanol / 18 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1.1: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; 4-methyl-morpholine / ethyl acetate; acetic acid butyl ester / 17.5 h / 0 °C / Inert atmosphere
2.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 1.5 h / 0 °C
2.2: 20 - 25 °C / pH > 10
View Scheme
Multi-step reaction with 2 steps
1.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / ethyl acetate; acetonitrile / 3 h
2.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 0.5 h / 0 °C
2.2: 18 h / 20 °C
View Scheme
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

(S)-N-Boc-3-fluoroadamantylglycine-L-cis-4,5-methanoprolinamide
361442-06-0

(S)-N-Boc-3-fluoroadamantylglycine-L-cis-4,5-methanoprolinamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 85 percent / EDAC; HOBT; TEA / dimethylformamide / 20 °C
2: 94 percent / diethylaminosulfur trifluoride / CH2Cl2 / 0.25 h / -78 °C
View Scheme
Multi-step reaction with 2 steps
1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; triethylamine / N,N-dimethyl-formamide / 0 - 20 °C
2: diethylamino-sulfur trifluoride / dichloromethane / 0.25 h / -78 °C / Inert atmosphere
View Scheme
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

(S)-3-fluoroadamantylglycine-L-cis-4,5-methanoprolinenitrile TFA salt

(S)-3-fluoroadamantylglycine-L-cis-4,5-methanoprolinenitrile TFA salt

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 85 percent / EDAC; HOBT; TEA / dimethylformamide / 20 °C
2: 94 percent / diethylaminosulfur trifluoride / CH2Cl2 / 0.25 h / -78 °C
3: 72 percent / CH2Cl2 / 0.5 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; triethylamine / N,N-dimethyl-formamide / 0 - 20 °C
2: diethylamino-sulfur trifluoride / dichloromethane / 0.25 h / -78 °C / Inert atmosphere
3: 1H-imidazole; pyridine; trichlorophosphate / 0.67 h / -30 °C / Inert atmosphere
4: dichloromethane / 0.5 h / 20 °C
View Scheme
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

(S)-3-hydroxyadamantylglycine-L-cis-4,5-methanoprolinenitrile TFA salt
361442-05-9

(S)-3-hydroxyadamantylglycine-L-cis-4,5-methanoprolinenitrile TFA salt

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 85 percent / EDAC; HOBT; TEA / dimethylformamide / 20 °C
2.1: pyridine; trifluoroacetic anhydride / tetrahydrofuran / 1 h
2.2: 92 percent / aq. KOH / methanol / 18 h / 20 °C
3.1: 95 percent / CH2Cl2 / 2.5 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1.1: benzotriazol-1-ol / dichloromethane / 0.08 h / -5 - 0 °C
1.2: 15.5 h / -7 - 10 °C
2.1: pyridine; trifluoroacetic anhydride / tetrahydrofuran / 6.33 h / -3 - 15 °C
2.2: 7 - 15 °C / pH 10 - 10.5
3.1: dichloromethane / -5 - 2 °C
View Scheme
Multi-step reaction with 4 steps
1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; triethylamine / N,N-dimethyl-formamide / 0 - 20 °C
2: N-ethyl-N,N-diisopropylamine / dichloromethane / 1.5 h / -78 - 0 °C / Inert atmosphere
3: 1H-imidazole; pyridine; trichlorophosphate / 0.75 h / -30 °C / Inert atmosphere
4: water / dichloromethane / 1.5 h / 0 °C
View Scheme

361442-00-4Relevant articles and documents

Preparation of an amino acid intermediate for the dipeptidyl Peptidase IV inhibitor, saxagliptin, using a modified phenylalanine dehydrogenase

Hanson, Ronald L.,Goldberg, Steven L.,Brzozowski, David B.,Tully, Thomas P.,Cazzulino, Dana,Parker, William L.,Lyngberg, Olav K.,Vu, True C.,Wong, Michael K.,Patel, Ramesh N.

, p. 1369 - 1378 (2007)

The non-proteinogenic amino acid 2-(3-hydroxy-1-adamantyl)-(2S)- aminoethanoic acid [2, (S)-3-hydroxyadamantylglycine], is a key intermediate required for the synthesis of Saxagliptin, a dipeptidyl peptidase IV inhibitor under development for treatment of type 2 diabetes mellitus. Keto acid 2-(3-hydroxy-1-adamantyl)-2-oxoethanoic acid (1) was converted to (S)-3-hydroxyadamantylglycine by reductive amination using a phenylalanine dehydrogenase from Thermoactinomyces intermedius expressed in a modified form in Pichia pastoris or Escherichia coli. NAD (nicotinamide adenine dinucleotide) produced during the reaction was recycled to NADH (reduced form of nicotinamide adenine dinucleotide) using formate dehydrogenase. Pichia pastoris produces an endogenous formate dehydrogenase when grown on methanol, and the corresponding gene was cloned and expressed in E. coli. The modified phenylalanine dehydrogenase contains two amino acid changes at the C-terminus and a 12-amino acid extension of the C-terminus. The modified enzyme is more effective with keto acid 1 than the wild-type enzyme, but less effective with the natural substrate, phenylpyruvate. Production of multi-kg batches was originally carried out with extracts of Pichia pastoris expressing the modified phenylalanine dehydrogenase from Thermoactinomyces intermedius and endogenous formate dehydrogenase, and further scaled up using a preparation of the two enzymes expressed in E. coli.

A process for preparing hydroxy adamantane glycine derivatives

-

, (2017/07/14)

The invention aims to provide a novel and simple synthesis route of a hydroxyadamantylglycine derivative represented by the formula I, namely (aS)-a-[[(1,1-dimethylethoxy)carboxyl]-amino]-1-(3-hydroxyadamantyl)-acetic acid) or salts of the derivative through developing a novel compound. A novel compound namely 2(aS)-a-amino-1-adamantyl-acetamide represented by the formula III is taken as the primary raw material and then is subjected to hydrolysis reactions and hydroxy group introduction so as to obtain the (aS)-a-[[(1,1-dimethylethoxy)carboxyl]-amino]-1-(3-hydroxyadamantyl)-acetic acid) represented by the formula I or salts of the derivative. The invention further provides a synthesis method of the novel compound represented by the formula III. The synthesis method can solve the disadvantages that the cost of enzyme catalyzed reactions is high, the enzyme catalyzed reactions are unstable, the chemical catalysis method has a low ee value, and the reaction product is not easy to purify in the prior art, and thus is more suitable for industrial production.

A facile and economic method for the synthesis of (S)-N-Boc-3′-hydroxyadamantylglycine

Li, Jie,Jiang, Xue,Gan, Run,Zhang, Ming,Pan, Xinmei,Hu, Xiangnan

, p. 5709 - 5721 (2016/06/01)

(S)-N-Boc-3′-hydroxyadamantylglycine (I) is an important intermediate of saxagliptin for type 2 diabetes mellitus (T2DM). It was prepared from 1-adamantanecarboxylic acid(1) via mild reaction with sulfuric acid/nitric acid, VHA reagent (SOCl2/DMF) and sodium diethyl malonate, then was treated with hydrolysis, decarboxylation, alkalization and oxidation to give 2-(3-hydroxy-1-adamantyl)-2-oxoacetic acid (4), then through oximation, reduction and (Boc)2O protection to give the N-Boc-3′-hydroxyadamantylglycine(6), then was treated with quinidine to get (S)- N-Boc-3′-hydroxyadamantylglycine(I) and quinine to get (R)–N-Boc-3′-hydroxyadamantylglycine(II). Finally, Compound II was racemized by dicyclohexylcarbodiimide (DCC) and sodium?hydride (NaH) to afford compound 6. In this route, the overall yield of preparing compound I was about 35?% and the enantiomeric excess (ee) reach to 99?%. This route provided a novel idea for the preparation of (S)-N-Boc-3′-hydroxyadamantylglycine.

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