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73286-70-1

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73286-70-1 Usage

Chemical Properties

White to yellow low melting solid or liquid

Uses

Used in a synthesis of ?-aryl-GABA analogues by Heck arylation with arenediazonium salts, as well as synthesize aryl pyrrolizidines. N-Boc-pyrroline has also been utilized in the synthesis of various antibacterial compounds. It has also been used in the preparation of regioisomeric 3-hydroxyisoxazolinyl prolines which are medicinally active.

General Description

N-Boc-2,5-dihydro-1H-pyrrole, also known as tert-butyl 2,5-dihydro-1H-pyrrole-1-carboxylate, can be synthesized from N-boc-diallylamine.

Check Digit Verification of cas no

The CAS Registry Mumber 73286-70-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,3,2,8 and 6 respectively; the second part has 2 digits, 7 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 73286-70:
(7*7)+(6*3)+(5*2)+(4*8)+(3*6)+(2*7)+(1*0)=141
141 % 10 = 1
So 73286-70-1 is a valid CAS Registry Number.
InChI:InChI=1/C9H15NO2/c1-9(2,3)12-8(11)10-6-4-5-7-10/h4,6H,5,7H2,1-3H3

73286-70-1 Well-known Company Product Price

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  • Alfa Aesar

  • (L20406)  N-Boc-3-pyrroline, 97%   

  • 73286-70-1

  • 1g

  • 1362.0CNY

  • Detail
  • Alfa Aesar

  • (L20406)  N-Boc-3-pyrroline, 97%   

  • 73286-70-1

  • 5g

  • 5340.0CNY

  • Detail
  • Aldrich

  • (477516)  N-Boc-2,5-dihydro-1H-pyrrole  96%

  • 73286-70-1

  • 477516-1G

  • 259.74CNY

  • Detail
  • Aldrich

  • (477516)  N-Boc-2,5-dihydro-1H-pyrrole  96%

  • 73286-70-1

  • 477516-5G

  • 1,016.73CNY

  • Detail

73286-70-1SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name N-Boc-pyrroline

1.2 Other means of identification

Product number -
Other names N-T-BOC-2,5-DIHYDROPYRROLE

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:73286-70-1 SDS

73286-70-1Synthetic route

3-Pyrroline
109-96-6

3-Pyrroline

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

N-(tert-butoxycarbonyl)-3-pyrroline
73286-70-1

N-(tert-butoxycarbonyl)-3-pyrroline

Conditions
ConditionsYield
In tetrahydrofuran; water at 0 - 20℃; for 3.16667h;100%
In dichloromethane at 0 - 20℃; Inert atmosphere;100%
In dichloromethane at 0 - 20℃; for 18.58h; Inert atmosphere;100%
tert-butyl diallylcarbamate
151259-38-0

tert-butyl diallylcarbamate

N-(tert-butoxycarbonyl)-3-pyrroline
73286-70-1

N-(tert-butoxycarbonyl)-3-pyrroline

Conditions
ConditionsYield
With Hoveyda-Grubbs catalyst second generation In toluene at 50℃; for 8h; Glove box;99%
With Grubbs catalyst first generation In dichloromethane for 2h; Inert atmosphere; Reflux;99%
[RuCl2(=CHCH3)(PCy3)2] In dichloromethane at 20℃; for 15h;98%
3-Pyrroline
109-96-6

3-Pyrroline

N-(tert-butyloxycarbonyl) azide
1070-19-5

N-(tert-butyloxycarbonyl) azide

N-(tert-butoxycarbonyl)-3-pyrroline
73286-70-1

N-(tert-butoxycarbonyl)-3-pyrroline

Conditions
ConditionsYield
With triethylamine In 1,4-dioxane; water at 50℃; for 15h;87.5%
3-Pyrroline
109-96-6

3-Pyrroline

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

A

N-(tert-butoxycarbonyl)-3-pyrroline
73286-70-1

N-(tert-butoxycarbonyl)-3-pyrroline

B

tert-butyl pyrrolidine-1-carboxylate
86953-79-9

tert-butyl pyrrolidine-1-carboxylate

Conditions
ConditionsYield
With pyrrolidine; sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; for 24h;A 87%
B n/a
In ethyl acetate at 0 - 20℃;A 63%
B 37%
In ethyl acetate at 0 - 10℃;
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

2,5-dihydro-1H-pyrrole hydrochloride
63468-63-3

2,5-dihydro-1H-pyrrole hydrochloride

N-(tert-butoxycarbonyl)-3-pyrroline
73286-70-1

N-(tert-butoxycarbonyl)-3-pyrroline

Conditions
ConditionsYield
With triethylamine In methanol at 0 - 20℃;85%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

poly(ethylene glycol)-3400 bis[p-({2-[(2,5-dihydro-1H-pyrrol-1-yl)sulfonyl]ethyl}dimethylsilyl)phenyl] ether

poly(ethylene glycol)-3400 bis[p-({2-[(2,5-dihydro-1H-pyrrol-1-yl)sulfonyl]ethyl}dimethylsilyl)phenyl] ether

N-(tert-butoxycarbonyl)-3-pyrroline
73286-70-1

N-(tert-butoxycarbonyl)-3-pyrroline

Conditions
ConditionsYield
With cesium fluoride In N,N-dimethyl-formamide at 110℃;80%
tert-butyl di(but-3-en-1-yl)carbamate
1211531-07-5

tert-butyl di(but-3-en-1-yl)carbamate

N-(tert-butoxycarbonyl)-3-pyrroline
73286-70-1

N-(tert-butoxycarbonyl)-3-pyrroline

Conditions
ConditionsYield
With Grubbs catalyst first generation In dichloromethane at 20℃; for 17h;73%
Z-1,4-dichlorobutene
1476-11-5

Z-1,4-dichlorobutene

tert-butyl carbamate
4248-19-5

tert-butyl carbamate

N-(tert-butoxycarbonyl)-3-pyrroline
73286-70-1

N-(tert-butoxycarbonyl)-3-pyrroline

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 20 - 50℃; for 5.66667h;60%
With sodium hydride In N,N-dimethyl-formamide57%
Stage #1: tert-butyl carbazate With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 1.25h;
Stage #2: Z-1,4-dichlorobutene In N,N-dimethyl-formamide; mineral oil at 80℃; for 5h;
tert-butyl thiomorpholine-4-carboxylic acid-1,1-dioxide
215791-95-0

tert-butyl thiomorpholine-4-carboxylic acid-1,1-dioxide

N-(tert-butoxycarbonyl)-3-pyrroline
73286-70-1

N-(tert-butoxycarbonyl)-3-pyrroline

Conditions
ConditionsYield
With 1,2-dibromo-1,1,2,2-tetrachloroethane; alumina-supported potassium hydroxide In tetrahydrofuran; tert-butyl alcohol at 20℃; for 4h; Ramberg-Baecklund Rearrangement;52%
Z-1,4-dichlorobutene
1476-11-5

Z-1,4-dichlorobutene

N-(tert-butoxycarbonyl)-3-pyrroline
73286-70-1

N-(tert-butoxycarbonyl)-3-pyrroline

Conditions
ConditionsYield
Stage #1: tert-butyl carbazate With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.166667h;
Stage #2: Z-1,4-dichlorobutene In N,N-dimethyl-formamide at 20 - 65℃; for 20.25h;
51%
(Z)-4-chlorobut-2-en-1-amine hydrochloride
54880-27-2

(Z)-4-chlorobut-2-en-1-amine hydrochloride

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

N-(tert-butoxycarbonyl)-3-pyrroline
73286-70-1

N-(tert-butoxycarbonyl)-3-pyrroline

Conditions
ConditionsYield
With potassium carbonate45%
1,4-dichloro-2-butene
764-41-0

1,4-dichloro-2-butene

tert-butyl carbamate
4248-19-5

tert-butyl carbamate

N-(tert-butoxycarbonyl)-3-pyrroline
73286-70-1

N-(tert-butoxycarbonyl)-3-pyrroline

Conditions
ConditionsYield
Stage #1: 1,4-dichloro-2-butene With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.166667h;
Stage #2: tert-butyl carbazate In N,N-dimethyl-formamide at 0 - 65℃;
45%
N-Boc-N-allyl-cis-cinnamylamine
219668-54-9

N-Boc-N-allyl-cis-cinnamylamine

N-(tert-butoxycarbonyl)-3-pyrroline
73286-70-1

N-(tert-butoxycarbonyl)-3-pyrroline

Conditions
ConditionsYield
With <(c-C6H11)2(c-Me2NClC5H9)P>2Cl2Ru=CHPh In methanol at 45℃; for 2h; Yield given;
N-Allyl-N-tert-butylcarbonyl-N-cinnamylamine
219668-51-6

N-Allyl-N-tert-butylcarbonyl-N-cinnamylamine

N-(tert-butoxycarbonyl)-3-pyrroline
73286-70-1

N-(tert-butoxycarbonyl)-3-pyrroline

Conditions
ConditionsYield
With <(c-C6H11)2(c-Me2NClC5H9)P>2Cl2Ru=CHPh In methanol at 45℃; for 30h; Yield given;
ortho-cresol
95-48-7

ortho-cresol

tert-butyl (3R)-3-methylsulfonyloxypyrrolidine-1-carboxylate
127423-61-4

tert-butyl (3R)-3-methylsulfonyloxypyrrolidine-1-carboxylate

A

C16H23O3N

C16H23O3N

B

N-(tert-butoxycarbonyl)-3-pyrroline
73286-70-1

N-(tert-butoxycarbonyl)-3-pyrroline

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 60℃; Title compound not separated from byproducts.;
ortho-cresol
95-48-7

ortho-cresol

(S)-tert-butyl 3-(methylsulfonyloxy)pyrrolidine-1-carboxylate
132945-75-6

(S)-tert-butyl 3-(methylsulfonyloxy)pyrrolidine-1-carboxylate

A

3-o-tolyloxy-pyrrolidine-1-carboxylic acid tert-butyl ester

3-o-tolyloxy-pyrrolidine-1-carboxylic acid tert-butyl ester

B

N-(tert-butoxycarbonyl)-3-pyrroline
73286-70-1

N-(tert-butoxycarbonyl)-3-pyrroline

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 60℃; Title compound not separated from byproducts.;
3-methyl-phenol
108-39-4

3-methyl-phenol

tert-butyl (3R)-3-methylsulfonyloxypyrrolidine-1-carboxylate
127423-61-4

tert-butyl (3R)-3-methylsulfonyloxypyrrolidine-1-carboxylate

A

C16H23O3N

C16H23O3N

B

N-(tert-butoxycarbonyl)-3-pyrroline
73286-70-1

N-(tert-butoxycarbonyl)-3-pyrroline

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 60℃; Title compound not separated from byproducts.;
3-methyl-phenol
108-39-4

3-methyl-phenol

(S)-tert-butyl 3-(methylsulfonyloxy)pyrrolidine-1-carboxylate
132945-75-6

(S)-tert-butyl 3-(methylsulfonyloxy)pyrrolidine-1-carboxylate

A

C16H23O3N

C16H23O3N

B

N-(tert-butoxycarbonyl)-3-pyrroline
73286-70-1

N-(tert-butoxycarbonyl)-3-pyrroline

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 60℃; Title compound not separated from byproducts.;
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

N-(tert-butoxycarbonyl)-3-pyrroline
73286-70-1

N-(tert-butoxycarbonyl)-3-pyrroline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 93 percent / cyclohexane
2: 98 percent / Cl2Ru(PCy3)2CHMe / CH2Cl2
View Scheme
Multi-step reaction with 2 steps
1: 98 percent / NH3 / ethanol / 0 - 20 °C
2: 60 percent / NaH / dimethylformamide / 5.67 h / 20 - 50 °C
View Scheme
Multi-step reaction with 2 steps
1: 93 percent / cyclohexane / 20 h / 20 °C
2: 98 percent / Cl2Ru(PCy3)2CHMe / CH2Cl2 / 15 h / 20 °C
View Scheme
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

pentacarbonyl<1-<<(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl>oxy>-(E)-3-phenyl-2-propenylidene>chromium

pentacarbonyl<1-<<(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl>oxy>-(E)-3-phenyl-2-propenylidene>chromium

N-(tert-butoxycarbonyl)-3-pyrroline
73286-70-1

N-(tert-butoxycarbonyl)-3-pyrroline

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 97 percent / CH2Cl2 / 8 h / 0 °C
2: 74 percent / NaH / dimethylformamide
3: <(c-C6H11)2(c-Me2NClC5H9)P>2Cl2Ru=CHPh / methanol / 2 h / 45 °C
View Scheme
Multi-step reaction with 3 steps
1: 97 percent / CH2Cl2 / 8 h / 0 °C
2: 80 percent / NaH / dimethylformamide / 16 h / 60 °C
3: <(c-C6H11)2(c-Me2NClC5H9)P>2Cl2Ru=CHPh / methanol / 30 h / 45 °C
View Scheme
N-tert-butoxycarbonylprop-2-en-1-amine
78888-18-3

N-tert-butoxycarbonylprop-2-en-1-amine

N-(tert-butoxycarbonyl)-3-pyrroline
73286-70-1

N-(tert-butoxycarbonyl)-3-pyrroline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 74 percent / NaH / dimethylformamide
2: <(c-C6H11)2(c-Me2NClC5H9)P>2Cl2Ru=CHPh / methanol / 2 h / 45 °C
View Scheme
Multi-step reaction with 2 steps
1: 80 percent / NaH / dimethylformamide / 16 h / 60 °C
2: <(c-C6H11)2(c-Me2NClC5H9)P>2Cl2Ru=CHPh / methanol / 30 h / 45 °C
View Scheme
pyrrolidine
123-75-1

pyrrolidine

3-Pyrroline
109-96-6

3-Pyrroline

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

A

N-(tert-butoxycarbonyl)-3-pyrroline
73286-70-1

N-(tert-butoxycarbonyl)-3-pyrroline

B

tert-butyl pyrrolidine-1-carboxylate
86953-79-9

tert-butyl pyrrolidine-1-carboxylate

Conditions
ConditionsYield
In ethyl acetate at 0 - 20℃;
In ethyl acetate at 0 - 20℃;
pyrrolidine
123-75-1

pyrrolidine

3-Pyrroline
109-96-6

3-Pyrroline

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

N-(tert-butoxycarbonyl)-3-pyrroline
73286-70-1

N-(tert-butoxycarbonyl)-3-pyrroline

Conditions
ConditionsYield
In tetrahydrofuran
In tetrahydrofuran
In tetrahydrofuran
3-Pyrroline
109-96-6

3-Pyrroline

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

A

2,2',5,5'-tetrahydro-1,1'-bipyrrole
1124345-33-0

2,2',5,5'-tetrahydro-1,1'-bipyrrole

B

N-(tert-butoxycarbonyl)-3-pyrroline
73286-70-1

N-(tert-butoxycarbonyl)-3-pyrroline

Conditions
ConditionsYield
In methanol at 25℃; for 25h; Large scale reaction;A n/a
B 57.5 kg
3-Pyrroline
109-96-6

3-Pyrroline

tert-butyldicarbonate
34619-03-9

tert-butyldicarbonate

N-(tert-butoxycarbonyl)-3-pyrroline
73286-70-1

N-(tert-butoxycarbonyl)-3-pyrroline

Conditions
ConditionsYield
In methanol
Z-1,4-dichlorobutene
1476-11-5

Z-1,4-dichlorobutene

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

N-(tert-butoxycarbonyl)-3-pyrroline
73286-70-1

N-(tert-butoxycarbonyl)-3-pyrroline

Conditions
ConditionsYield
With potassium carbonate In methanol Delepine reactions;
tert-butyl thiomorpholine-4-carboxylate
220655-09-4

tert-butyl thiomorpholine-4-carboxylate

N-(tert-butoxycarbonyl)-3-pyrroline
73286-70-1

N-(tert-butoxycarbonyl)-3-pyrroline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 - 20 °C
2: 1,2-dibromo-1,1,2,2-tetrachloroethane; alumina-supported potassium hydroxide / tetrahydrofuran; tert-butyl alcohol / 4 h / 20 °C
View Scheme
N-(tert-butoxycarbonyl)-3-pyrroline
73286-70-1

N-(tert-butoxycarbonyl)-3-pyrroline

1-tert-butoxycarbonyl-3,4-epoxypyrrolidine
114214-49-2

1-tert-butoxycarbonyl-3,4-epoxypyrrolidine

Conditions
ConditionsYield
With Oxone; ethylenediaminetetraacetic acid In various solvent(s)100%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 12h;100%
Stage #1: N-(tert-butoxycarbonyl)-3-pyrroline With N-Bromosuccinimide In water; dimethyl sulfoxide at 0 - 25℃; for 4h;
Stage #2: With sodium hydroxide In water; dimethyl sulfoxide at 20℃; for 3h; Solvent; Temperature;
96%
N-(tert-butoxycarbonyl)-3-pyrroline
73286-70-1

N-(tert-butoxycarbonyl)-3-pyrroline

3-Pyrroline
109-96-6

3-Pyrroline

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 25℃; for 4h;100%
With trifluoroacetic acid In dichloromethane at 25℃; for 4h;
With trifluoroacetic acid In dichloromethane at 20℃; for 1h;
N-(tert-butoxycarbonyl)-3-pyrroline
73286-70-1

N-(tert-butoxycarbonyl)-3-pyrroline

(±)-trans-tert-butyl 3-bromo-4-hydroxypyrrolidine-1-carboxylate

(±)-trans-tert-butyl 3-bromo-4-hydroxypyrrolidine-1-carboxylate

Conditions
ConditionsYield
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; water In acetonitrile100%
With N-Bromosuccinimide In water; dimethyl sulfoxide at 0 - 25℃; for 17h;74%
With N-Bromosuccinimide In water; dimethyl sulfoxide at 20℃; for 2h;
N-(tert-butoxycarbonyl)-3-pyrroline
73286-70-1

N-(tert-butoxycarbonyl)-3-pyrroline

trans tert-butyl 3,4-dihydroxypyrrolidine-1-carboxylate
298681-10-4

trans tert-butyl 3,4-dihydroxypyrrolidine-1-carboxylate

Conditions
ConditionsYield
Stage #1: With osmium(VIII) oxide; 4-methylmorpholine N-oxide In water; acetone for 0.5h;
Stage #2: N-(tert-butoxycarbonyl)-3-pyrroline In water; acetone for 20h;
100%
With osmium(VIII) oxide; 4-methylmorpholine N-oxide In tetrahydrofuran; tert-butyl alcohol at 20℃; for 4h;51%
With osmium(VIII) oxide; 4-methylmorpholine N-oxide In water at 20 - 25℃; for 5h;
With osmium(VIII) oxide; 4-methylmorpholine N-oxide In acetone at 20℃; for 18h;
With osmium(VIII) oxide; 4-methylmorpholine N-oxide In tetrahydrofuran; water at 0 - 20℃; for 18h; Inert atmosphere;4.31 g
N-(tert-butoxycarbonyl)-3-pyrroline
73286-70-1

N-(tert-butoxycarbonyl)-3-pyrroline

tert-butyl pyrrolidine-1-carboxylate
86953-79-9

tert-butyl pyrrolidine-1-carboxylate

Conditions
ConditionsYield
With tetrahydroxydiboron; palladium 10% on activated carbon; water In dichloromethane at 20℃; for 60h; Inert atmosphere;97%
With water; palladium diacetate; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In dichloromethane at 25℃; for 12h; Sealed tube; Inert atmosphere; chemoselective reaction;87%
N-(tert-butoxycarbonyl)-3-pyrroline
73286-70-1

N-(tert-butoxycarbonyl)-3-pyrroline

ethylene glycol
107-21-1

ethylene glycol

3-bromo-4-(2-hydroxyethoxy)pyrrolidine-1-carboxylic acid tert-butyl ester
1358783-14-8

3-bromo-4-(2-hydroxyethoxy)pyrrolidine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With N-Bromosuccinimide for 18h;97%
With N-Bromosuccinimide In 1,2-dimethoxyethane at 20℃; for 16h;89.11%
With N-Bromosuccinimide at 20℃; for 0.333333h; Darkness;60%
With N-Bromosuccinimide at 15℃; for 16h; Inert atmosphere;
N-(tert-butoxycarbonyl)-3-pyrroline
73286-70-1

N-(tert-butoxycarbonyl)-3-pyrroline

rac-trans-3-bromo-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester

rac-trans-3-bromo-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With N-Bromosuccinimide; water In dimethyl sulfoxide at 0 - 20℃; for 2h;95%
Bromoform
75-25-2

Bromoform

N-(tert-butoxycarbonyl)-3-pyrroline
73286-70-1

N-(tert-butoxycarbonyl)-3-pyrroline

tert-butyl 6,6-dibromo-3-azabicyclo[3.1.0]hexane-3-carboxylate

tert-butyl 6,6-dibromo-3-azabicyclo[3.1.0]hexane-3-carboxylate

Conditions
ConditionsYield
With sodium tert-pentoxide In n-heptane at -10 - 0℃; for 6h; Reagent/catalyst; Temperature; Solvent; Inert atmosphere; Large scale;95%
With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In ethanol; dichloromethane; water at 40 - 50℃; for 18h;35%
With N-benzyl-N,N,N-triethylammonium chloride; potassium hydroxide In dichloromethane; water at 0 - 20℃; for 2h; Inert atmosphere;
With N-benzyl-N,N,N-triethylammonium chloride; potassium hydroxide In dichloromethane at 25℃; for 12h; Inert atmosphere;
2,2-dichloropropane
594-20-7

2,2-dichloropropane

N-(tert-butoxycarbonyl)-3-pyrroline
73286-70-1

N-(tert-butoxycarbonyl)-3-pyrroline

C12H21NO2

C12H21NO2

Conditions
ConditionsYield
Stage #1: N-(tert-butoxycarbonyl)-3-pyrroline With C29H35Br2CoN3; zinc dibromide; zinc In tetrahydrofuran at 22℃; for 0.25h; Simmons-Smith Cyclopropanation; Inert atmosphere; Glovebox;
Stage #2: 2,2-dichloropropane In tetrahydrofuran at 22℃; for 24h; Simmons-Smith Cyclopropanation; Inert atmosphere; Glovebox; regioselective reaction;
91%
N,N-dibenzylformamide
5464-77-7

N,N-dibenzylformamide

N-(tert-butoxycarbonyl)-3-pyrroline
73286-70-1

N-(tert-butoxycarbonyl)-3-pyrroline

tert-butyl (1R,5S,6s)-6-(N,N-dibenzylamino)-3-azabicyclo[3.1.0]hexane-3-carboxylate
497163-57-2

tert-butyl (1R,5S,6s)-6-(N,N-dibenzylamino)-3-azabicyclo[3.1.0]hexane-3-carboxylate

Conditions
ConditionsYield
With titanium(IV) isopropylate; methylmagnesium chloride; cyclohexylmagnesium bromide In tetrahydrofuran; diethyl ether for 0.25h; Heating;90%
Stage #1: N-(tert-butoxycarbonyl)-3-pyrroline With titanium(IV) isopropylate; methylmagnesium chloride In tetrahydrofuran at 5 - 10℃; for 3h; Large scale;
Stage #2: N,N-dibenzylformamide In tetrahydrofuran at 10 - 35℃; for 3.5h; Large scale;
Stage #3: With cyclohexylmagnesium bromide In tetrahydrofuran; 2-methyltetrahydrofuran at 30 - 40℃; for 10h; Large scale;
35%
1-(1,1,1-trifluoroprop-2-en-2-yl)-4-methoxybenzene
69843-08-9

1-(1,1,1-trifluoroprop-2-en-2-yl)-4-methoxybenzene

N-(tert-butoxycarbonyl)-3-pyrroline
73286-70-1

N-(tert-butoxycarbonyl)-3-pyrroline

tert-butyl 2-(3,3-difluoro-2-(4-methoxyphenyl)allyl)pyrrolidine-1-carboxylate

tert-butyl 2-(3,3-difluoro-2-(4-methoxyphenyl)allyl)pyrrolidine-1-carboxylate

Conditions
ConditionsYield
With 6,6'-dimethyl-2,2'-bipyridine; (1,2-dimethoxyethane)dichloronickel(II); Triethoxysilane; lithium fluoride In dimethyl sulfoxide at 60℃; for 24h; Inert atmosphere; Sealed tube; chemoselective reaction;89%
N-(tert-butoxycarbonyl)-3-pyrroline
73286-70-1

N-(tert-butoxycarbonyl)-3-pyrroline

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

1-(tert-butoxycarbonyl)-2,5-dihydro-1H-pyrrole-2-carboxylic acid methyl ester
202477-57-4

1-(tert-butoxycarbonyl)-2,5-dihydro-1H-pyrrole-2-carboxylic acid methyl ester

Conditions
ConditionsYield
With lithium diisopropyl amide In tetrahydrofuran at 0℃;87%
With lithium diisopropyl amide In tetrahydrofuran; n-heptane; ethylbenzene at 5℃; for 1h;83%
With lithium diisopropyl amide In tetrahydrofuran at -78 - 0℃; for 2h;
N-(tert-butoxycarbonyl)-3-pyrroline
73286-70-1

N-(tert-butoxycarbonyl)-3-pyrroline

benzohydroximoyl chloride
698-16-8

benzohydroximoyl chloride

tert-butyl 3-phenyl-6,6a-dihydro-3aH-pyrrolo[3,4-d]isoxazole-5(4H)-carboxylate
1253183-36-6

tert-butyl 3-phenyl-6,6a-dihydro-3aH-pyrrolo[3,4-d]isoxazole-5(4H)-carboxylate

Conditions
ConditionsYield
With potassium carbonate In ethyl acetate at 90℃; for 0.166667h;87%
With potassium carbonate In ethyl acetate at 90℃; under 5171.62 Torr; for 0.166667h; Inert atmosphere;69%
N-(tert-butoxycarbonyl)-3-pyrroline
73286-70-1

N-(tert-butoxycarbonyl)-3-pyrroline

rac-tert-butyl (1R,5S)-6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate
114214-49-2

rac-tert-butyl (1R,5S)-6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃;86%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 24h;82%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 12h; Inert atmosphere;75%
formaldehyd
50-00-0

formaldehyd

N-benzylhydroxylamine hydrochloride
29601-98-7

N-benzylhydroxylamine hydrochloride

N-(tert-butoxycarbonyl)-3-pyrroline
73286-70-1

N-(tert-butoxycarbonyl)-3-pyrroline

(+/-)-1,1-dimethylethyl-2-(phenylmethyl)hexahydro-5H-pyrrolo[3,4-d]isoxazole-5-carboxylate

(+/-)-1,1-dimethylethyl-2-(phenylmethyl)hexahydro-5H-pyrrolo[3,4-d]isoxazole-5-carboxylate

Conditions
ConditionsYield
With triethylamine In ethanol; toluene at 80℃; for 24h;85%
formaldehyd
50-00-0

formaldehyd

N-benzylhydroxylamine hydrochloride
29601-98-7

N-benzylhydroxylamine hydrochloride

N-(tert-butoxycarbonyl)-3-pyrroline
73286-70-1

N-(tert-butoxycarbonyl)-3-pyrroline

1,1-dimethylethyl-2-(phenylmethyl)hexahydro-5H-pyrrolo[3,4-d]isoxazole-5-carboxylate

1,1-dimethylethyl-2-(phenylmethyl)hexahydro-5H-pyrrolo[3,4-d]isoxazole-5-carboxylate

Conditions
ConditionsYield
With triethylamine In ethanol; toluene at 80℃; for 24h;85%
1-(3-iodopropoxy)benzene
20549-68-2

1-(3-iodopropoxy)benzene

N-(tert-butoxycarbonyl)-3-pyrroline
73286-70-1

N-(tert-butoxycarbonyl)-3-pyrroline

tert-butyl 2-(3-phenoxypropyl)pyrrolidine-1-carboxylate

tert-butyl 2-(3-phenoxypropyl)pyrrolidine-1-carboxylate

Conditions
ConditionsYield
With potassium fluoride; nickel(II) iodide hydrate; diethoxymethylane; C16H16N2O In N,N-dimethyl acetamide at 25℃; Inert atmosphere; Sealed tube; regioselective reaction;84%
N-dibromomethylidenehydroxylamine
74213-24-4

N-dibromomethylidenehydroxylamine

N-(tert-butoxycarbonyl)-3-pyrroline
73286-70-1

N-(tert-butoxycarbonyl)-3-pyrroline

tert-butyl (+/-)-3-bromo-3a,4,6,6a-tetrahydro-5H-pyrrolo[3,4-d]isoxazole-5-carboxylate

tert-butyl (+/-)-3-bromo-3a,4,6,6a-tetrahydro-5H-pyrrolo[3,4-d]isoxazole-5-carboxylate

Conditions
ConditionsYield
With sodium hydrogencarbonate In ethyl acetate for 72h;82%
With sodium hydrogencarbonate In ethyl acetate at 20℃; for 72h; Cycloaddition;80.7%
(trifluoromethyl)trimethylsilane
81290-20-2

(trifluoromethyl)trimethylsilane

N-(tert-butoxycarbonyl)-3-pyrroline
73286-70-1

N-(tert-butoxycarbonyl)-3-pyrroline

tert-butyl 6,6-difluoro-3-azabicyclo[3.1.0]hexane-3-carboxylate

tert-butyl 6,6-difluoro-3-azabicyclo[3.1.0]hexane-3-carboxylate

Conditions
ConditionsYield
With sodium iodide In tetrahydrofuran at 65℃; Inert atmosphere;81%
With sodium iodide In tetrahydrofuran for 8h; Reflux;67%
(2-iodopropyl)benzene
29527-87-5

(2-iodopropyl)benzene

N-(tert-butoxycarbonyl)-3-pyrroline
73286-70-1

N-(tert-butoxycarbonyl)-3-pyrroline

(±)-tert-butyl 2-(1-phenylpropan-2-yl)pyrrolidine-1-carboxylate

(±)-tert-butyl 2-(1-phenylpropan-2-yl)pyrrolidine-1-carboxylate

Conditions
ConditionsYield
With potassium fluoride; nickel(II) iodide hydrate; diethoxymethylane; C16H16N2O In N,N-dimethyl acetamide at 25℃; Inert atmosphere; Sealed tube;81%
N-(tert-butoxycarbonyl)-3-pyrroline
73286-70-1

N-(tert-butoxycarbonyl)-3-pyrroline

tert-butyl 3-bromo-4-hydroxypyrrolidine-1-carboxylate
1017782-17-0

tert-butyl 3-bromo-4-hydroxypyrrolidine-1-carboxylate

Conditions
ConditionsYield
With N-Bromosuccinimide In water; dimethyl sulfoxide at 0 - 25℃; for 4h; Inert atmosphere;78%
With N-Bromosuccinimide; water In dimethyl sulfoxide at 0 - 20℃; for 4.5h;
With N-Bromosuccinimide; water In dimethyl sulfoxide at 0 - 20℃; for 2h;5 g
Methanesulfenyl chloride
5813-48-9

Methanesulfenyl chloride

N-(tert-butoxycarbonyl)-3-pyrroline
73286-70-1

N-(tert-butoxycarbonyl)-3-pyrroline

methylamine
74-89-5

methylamine

trans-1-N-tert-butoxycarbonyl-3-methylamino-4-methylthiopyrrolidine

trans-1-N-tert-butoxycarbonyl-3-methylamino-4-methylthiopyrrolidine

Conditions
ConditionsYield
Stage #1: Methanesulfenyl chloride; N-(tert-butoxycarbonyl)-3-pyrroline In dichloromethane at 20℃; for 24h;
Stage #2: methylamine In tetrahydrofuran; water at 70℃; for 15h;
77%
N-(tert-butoxycarbonyl)-3-pyrroline
73286-70-1

N-(tert-butoxycarbonyl)-3-pyrroline

rac-tert-butyl (3R,4S)-3,4-dihydroxypyrrolidine-1-carboxylate

rac-tert-butyl (3R,4S)-3,4-dihydroxypyrrolidine-1-carboxylate

Conditions
ConditionsYield
With osmium(VIII) oxide; 4-methylmorpholine N-oxide In water; acetone at 20℃; for 5h;77%
With osmium(VIII) oxide; 4-methylmorpholine N-oxide In tetrahydrofuran; water at 28℃; for 16h;61.06%
With osmium(VIII) oxide; water; 4-methylmorpholine N-oxide In tetrahydrofuran at 20℃;59%
N-(tert-butoxycarbonyl)-3-pyrroline
73286-70-1

N-(tert-butoxycarbonyl)-3-pyrroline

6-isopropyl-4,9-dimethyl-3-oxo-1,4-diazaspiro[4.5]dec-1-ene 1-oxide
188858-92-6

6-isopropyl-4,9-dimethyl-3-oxo-1,4-diazaspiro[4.5]dec-1-ene 1-oxide

A

(1S,2S,5R,3'aR,3'bS,7'aS)-2'-t-butoxycarbonyl-2-isopropyl-5,5'-dimethyl-1H-decahydro-spiro[cyclohexane-1,6'-7'-oxa-2',5',6'a-triazacyclopenta[a]pentalen-4'-one]

(1S,2S,5R,3'aR,3'bS,7'aS)-2'-t-butoxycarbonyl-2-isopropyl-5,5'-dimethyl-1H-decahydro-spiro[cyclohexane-1,6'-7'-oxa-2',5',6'a-triazacyclopenta[a]pentalen-4'-one]

B

(1S,2S,5R,3'aR,3'bS,7'aS)-1'-t-butoxycarbonyl-2-isopropyl-5,5'-dimethyl-1H-decahydro-spiro[cyclohexane-1,6'-7'-oxa-2',5',6'a-triazacyclopenta[a]pentalen-4'-one]

(1S,2S,5R,3'aR,3'bS,7'aS)-1'-t-butoxycarbonyl-2-isopropyl-5,5'-dimethyl-1H-decahydro-spiro[cyclohexane-1,6'-7'-oxa-2',5',6'a-triazacyclopenta[a]pentalen-4'-one]

Conditions
ConditionsYield
In toluene at 140℃; for 10.5h; Inert atmosphere; Sealed tube; Microwave irradiation; enantioselective reaction;A 21%
B 74%

73286-70-1Relevant articles and documents

Merging Halogen-Atom Transfer (XAT) and Cobalt Catalysis to Override E2-Selectivity in the Elimination of Alkyl Halides: A Mild Route towardcontra-Thermodynamic Olefins

Zhao, Huaibo,McMillan, Alastair J.,Constantin, Timothée,Mykura, Rory C.,Juliá, Fabio,Leonori, Daniele

supporting information, p. 14806 - 14813 (2021/09/18)

We report here a mechanistically distinct tactic to carry E2-type eliminations on alkyl halides. This strategy exploits the interplay of α-aminoalkyl radical-mediated halogen-atom transfer (XAT) with desaturative cobalt catalysis. The methodology is high-yielding, tolerates many functionalities, and was used to access industrially relevant materials. In contrast to thermal E2 eliminations where unsymmetrical substrates give regioisomeric mixtures, this approach enables, by fine-tuning of the electronic and steric properties of the cobalt catalyst, to obtain high olefin positional selectivity. This unprecedented mechanistic feature has allowed access tocontra-thermodynamic olefins, elusive by E2 eliminations.

A Scalable Membrane Pervaporation Approach for Continuous Flow Olefin Metathesis

Breen, Christopher P.,Parrish, Christine,Shangguan, Ning,Majumdar, Sudip,Murnen, Hannah,Jamison, Timothy F.,Bio, Matthew M.

supporting information, p. 2298 - 2303 (2020/05/14)

The translation of olefin metathesis reactions from the laboratory to process scale has been challenging with traditional batch techniques. In this contribution, we describe a continuous membrane reactor design that selectively permeates the ethylene byproduct from metathetical processes, thereby overcoming the mass-transport limitations that have negatively influenced the efficiency of this transformation in batch vessels. The membrane sheet-in-frame pervaporation module yielded turnover numbers of >7500 in the case of diethyl diallylmalonate ring-closing metathesis. The preparation of more challenging, low-effective-molarity substrates, a cyclooctene and a 14-membered macrocyclic lactone, was also effective. A comparison of optimal membrane reactor conditions to a sealed tubular reactor revealed that the benefits of ethylene removal are most apparent at low reaction concentrations.

JAK inhibitor compound and application thereof

-

Paragraph 0508; 0515; 0526-0527, (2020/09/12)

The invention relates to a JAK inhibitor compound and application thereof. Specifically, the invention discloses a compound shown as a formula (G), or an isotope labeled compound, or an optical isomer, a geometrical isomer, a tautomer or an isomer mixture of the compound, or a pharmaceutically acceptable salt of the compound, or a prodrug of the compound, or a metabolite of the compound. The invention also relates to the medical application of the compound.

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