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361440-67-7

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Basic Information
CAS No.: 361440-67-7
Name: (1S,3S,5S)-3-(Aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester
Article Data: 10
Molecular Structure:
Molecular Structure of 361440-67-7 ((1S,3S,5S)-3-(Aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester)
Formula: C11H18N2O3
Molecular Weight: 226.276
Synonyms: Saxagliptin Intermediate; 2-Azabicyclo[3.1.0]hexane-2-carboxylic acid, 3-(aminocarbonyl)-, 1,1-dimethylethyl ester, (1S,3S,5S)-; (1S,3S,5S)-3-(Aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester; (1S,3S,5S)-3-aminocarbonyl-2-azabicyclo[3.1.0]hexane-2-carboxylic acid, 1,1-dimethylethyl ester; (1S,3S,5S)-3-(Amino carbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester; (1S,3S,5S)-tert-Butyl 3-carbamoyl-2-azabicyclo[3.1.0]hexane-2-carboxylate; (1s,3s,5s)-3-(aminocarbonyl)-2-azabicyclo(3.1.0)hexane-2-carboxylic acid tert-butyl
EINECS: 1308068-626-2
Density: 1.228 g/cm3
Boiling Point: 388.9 °C at 760 mmHg
Flash Point: 189.024 °C
PSA: 72.63000
LogP: 1.50780
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361440-67-7

[1S-(1α,3β,5α)]-3-(aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid 1,1-dimethylethyl ester

Conditions
ConditionsYield
With n-butyllithium; C40H54NiP2 In tetrahydrofuran; hexane at 0 - 20℃; for 16h; Reagent/catalyst; Solvent; Inert atmosphere;93%
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(1S,3S,5S)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid

361440-67-7

[1S-(1α,3β,5α)]-3-(aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid 1,1-dimethylethyl ester

Conditions
ConditionsYield
Stage #1: (1S,3S,5S)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at -15℃; for 0.5h;
Stage #2: With ammonia In tetrahydrofuran; 1,4-dioxane at -30 - 20℃;		84%
Stage #1: (1S,3S,5S)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at -15℃; for 0.583333h;
Stage #2: With ammonia In tetrahydrofuran; 1,4-dioxane at -30 - 20℃;		84%
Stage #1: (1S,3S,5S)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid With C17H28N2O5; isobutyl chloroformate In tetrahydrofuran at -15℃; for 0.583333h; Inert atmosphere;
Stage #2: With ammonia In tetrahydrofuran; 1,4-dioxane at -30 - 20℃; Inert atmosphere;		84%
Stage #1: (1S,3S,5S)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid With methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at -20℃; for 0.5h; Inert atmosphere;
Stage #2: With ammonia In tetrahydrofuran at -5 - 20℃; for 3h;		9.84 g
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

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diiodomethane

361440-67-7

[1S-(1α,3β,5α)]-3-(aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid 1,1-dimethylethyl ester

Conditions
ConditionsYield
Stage #1: (5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester; diiodomethane With diethylzinc In water; ethyl acetate; toluene at -10 - 0℃; for 105h; Inert atmosphere;
Stage #2: With trifluoroacetic acid In water; ethyl acetate; toluene at -10 - 16℃; for 1.66667h; Reagent/catalyst; Inert atmosphere;		70%
Stage #1: diiodomethane With copper(I) bromide; zinc In tert-butyl methyl ether at 20℃; for 0.5h; Simmons-Smith Cyclopropanation; Inert atmosphere;
Stage #2: (5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester In tert-butyl methyl ether at 20℃; for 4.5h; Simmons-Smith Cyclopropanation; Inert atmosphere;		68%
Stage #1: diiodomethane With diethylzinc In 1,2-dimethoxyethane; dichloromethane; toluene at -30 - -25℃; for 0.75h; Simmons-Smith Reaction;
Stage #2: (5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester In 1,2-dimethoxyethane; dichloromethane; toluene at 22 - 24℃;
Stage #3: With sodium hydrogencarbonate In 1,2-dimethoxyethane; dichloromethane; water; toluene at 15℃; for 1h;		55%
With diethylzinc In 1,2-dimethoxyethane; dichloromethane at -30 - 20℃; Simmons-Smith Cyclopropanation; stereoselective reaction;45%
Stage #1: diiodomethane With diethylzinc In 1,2-dimethoxyethane; dichloromethane; toluene at -30 - -20℃; for 0.75h; Large scale;
Stage #2: (5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester In 1,2-dimethoxyethane; dichloromethane; toluene at -25 - 24℃; Large scale;
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di-tert-butyl dicarbonate

361440-67-7

[1S-(1α,3β,5α)]-3-(aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid 1,1-dimethylethyl ester

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: dmap
2: lithium triethylborohydride / toluene / -70 - -60 °C
3: dmap; trifluoroacetic anhydride; N-ethyl-N,N-diisopropylamine
4: water; lithium hydroxide / ethanol
5: ammonia; N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / tetrahydrofuran
6: diethylzinc / 1,2-dimethoxyethane; dichloromethane / -30 - 20 °C
View Scheme
Multi-step reaction with 5 steps
1.1: dmap / dichloromethane / 6 h / 20 °C
2.1: lithium triethylborohydride / tetrahydrofuran; toluene / 3 h / -78 °C
2.2: -78 °C
2.3: 2 h / -78 - 20 °C
3.1: diethylzinc / 1,2-dichloro-ethane / 19 h / -15 °C
4.1: lithium hydroxide; water / methanol / 20 h / 20 - 50 °C
5.1: C17H28N2O5; isobutyl chloroformate / tetrahydrofuran / 0.58 h / -15 °C / Inert atmosphere
5.2: -30 - 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 5 steps
1.1: dmap / toluene / 3 h / 25 °C / Large scale
2.1: lithium triethylborohydride / toluene; tetrahydrofuran / 0.5 h / -45 °C / Large scale
2.2: 3 h / 25 °C / Large scale
3.1: lithium hydroxide monohydrate / water; ethanol / 2 h / 25 °C / Large scale
4.1: methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / -25 - -20 °C / Large scale
4.2: 3 h / 0 - 20 °C / Large scale
5.1: diethylzinc / dichloromethane; toluene; 1,2-dimethoxyethane / 0.75 h / -30 - -20 °C / Large scale
5.2: -25 - 24 °C / Large scale
View Scheme
194594-23-5

5-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester

361440-67-7

[1S-(1α,3β,5α)]-3-(aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid 1,1-dimethylethyl ester

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: dmap; trifluoroacetic anhydride; N-ethyl-N,N-diisopropylamine
2: water; lithium hydroxide / ethanol
3: ammonia; N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / tetrahydrofuran
4: diethylzinc / 1,2-dimethoxyethane; dichloromethane / -30 - 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: N-ethyl-N,N-diisopropylamine; trifluoroacetic anhydride / toluene / 3 h / 15 - 80 °C
2.1: copper(I) bromide; trifluoroacetic acid; zinc / tetrahydrofuran / 18 h / 25 - 50 °C / Inert atmosphere
3.1: lithium hydroxide / ethanol; water / 6 h / 35 °C
4.1: N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / tetrahydrofuran / 0.5 h / -20 °C / Inert atmosphere
4.2: 3 h / -5 - 20 °C
View Scheme
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(S)-ethyl N-tert-butoxycarbonylpyroglutamate

361440-67-7

[1S-(1α,3β,5α)]-3-(aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid 1,1-dimethylethyl ester

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: lithium triethylborohydride / toluene / -70 - -60 °C
2: dmap; trifluoroacetic anhydride; N-ethyl-N,N-diisopropylamine
3: water; lithium hydroxide / ethanol
4: ammonia; N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / tetrahydrofuran
5: diethylzinc / 1,2-dimethoxyethane; dichloromethane / -30 - 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: lithium triethylborohydride / tetrahydrofuran; toluene / 3 h / -78 °C
1.2: -78 °C
1.3: 2 h / -78 - 20 °C
2.1: diethylzinc / 1,2-dichloro-ethane / 19 h / -15 °C
3.1: lithium hydroxide; water / methanol / 20 h / 20 - 50 °C
4.1: C17H28N2O5; isobutyl chloroformate / tetrahydrofuran / 0.58 h / -15 °C / Inert atmosphere
4.2: -30 - 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1.1: lithium triethylborohydride / toluene; tetrahydrofuran / 0.5 h / -45 °C / Large scale
1.2: 3 h / 25 °C / Large scale
2.1: lithium hydroxide monohydrate / water; ethanol / 2 h / 25 °C / Large scale
3.1: methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / -25 - -20 °C / Large scale
3.2: 3 h / 0 - 20 °C / Large scale
4.1: diethylzinc / dichloromethane; toluene; 1,2-dimethoxyethane / 0.75 h / -30 - -20 °C / Large scale
4.2: -25 - 24 °C / Large scale
View Scheme
7149-65-7

ethyl (S)-pyroglutamate

361440-67-7

[1S-(1α,3β,5α)]-3-(aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid 1,1-dimethylethyl ester

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: dmap
2: lithium triethylborohydride / toluene / -70 - -60 °C
3: dmap; trifluoroacetic anhydride; N-ethyl-N,N-diisopropylamine
4: water; lithium hydroxide / ethanol
5: ammonia; N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / tetrahydrofuran
6: diethylzinc / 1,2-dimethoxyethane; dichloromethane / -30 - 20 °C
View Scheme
Multi-step reaction with 5 steps
1.1: dmap / dichloromethane / 6 h / 20 °C
2.1: lithium triethylborohydride / tetrahydrofuran; toluene / 3 h / -78 °C
2.2: -78 °C
2.3: 2 h / -78 - 20 °C
3.1: diethylzinc / 1,2-dichloro-ethane / 19 h / -15 °C
4.1: lithium hydroxide; water / methanol / 20 h / 20 - 50 °C
5.1: C17H28N2O5; isobutyl chloroformate / tetrahydrofuran / 0.58 h / -15 °C / Inert atmosphere
5.2: -30 - 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 5 steps
1.1: dmap / toluene / 3 h / 25 °C / Large scale
2.1: lithium triethylborohydride / toluene; tetrahydrofuran / 0.5 h / -45 °C / Large scale
2.2: 3 h / 25 °C / Large scale
3.1: lithium hydroxide monohydrate / water; ethanol / 2 h / 25 °C / Large scale
4.1: methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / -25 - -20 °C / Large scale
4.2: 3 h / 0 - 20 °C / Large scale
5.1: diethylzinc / dichloromethane; toluene; 1,2-dimethoxyethane / 0.75 h / -30 - -20 °C / Large scale
5.2: -25 - 24 °C / Large scale
View Scheme
178172-26-4

(5S)-4,5-dihydro-1H-pyrrol-1,5-dicarboxylic acid [1-(1,1-dimethylethyl)] 5-ethyl ester

361440-67-7

[1S-(1α,3β,5α)]-3-(aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid 1,1-dimethylethyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: water; lithium hydroxide / ethanol
2: ammonia; N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / tetrahydrofuran
3: diethylzinc / 1,2-dimethoxyethane; dichloromethane / -30 - 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: isopropyl alcohol / 3 h / 50 °C / Inert atmosphere
2.1: ethyl acetate / 0.25 h / 8 °C / Inert atmosphere
2.2: 2 h / 8 - 12 °C / Inert atmosphere
3.1: ammonium hydroxide / 0.5 h / 0 - 20 °C
4.1: diethylzinc / ethyl acetate; water; toluene / 105 h / -10 - 0 °C / Inert atmosphere
4.2: 1.67 h / -10 - 16 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1.1: sodium hydroxide
2.1: sodium hydroxide / water
3.1: ammonium hydroxide / Inert atmosphere
4.1: diethylzinc / ethyl acetate; water; toluene / 105 h / -10 - 0 °C / Inert atmosphere
4.2: 1.67 h / -10 - 16 °C / Inert atmosphere
View Scheme
709031-37-8

(S)-1-(tert-butoxycarbonyl)-2,3-dihydro-1H-pyrrole-2-carboxylic acid diisopropylethylamine salt

361440-67-7

[1S-(1α,3β,5α)]-3-(aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid 1,1-dimethylethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: ammonia; N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / tetrahydrofuran
2: diethylzinc / 1,2-dimethoxyethane; dichloromethane / -30 - 20 °C
View Scheme
709031-41-4

4,5-duhydro-1H-pyrrole-1,5-dicarboxylic acid, 1-(1,1-dimethylethyl) dicyclohexylamine salt

361440-67-7

[1S-(1α,3β,5α)]-3-(aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid 1,1-dimethylethyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium hydroxide / water
2.1: ammonium hydroxide / Inert atmosphere
3.1: diethylzinc / ethyl acetate; water; toluene / 105 h / -10 - 0 °C / Inert atmosphere
3.2: 1.67 h / -10 - 16 °C / Inert atmosphere
View Scheme
Raw Materials
75-11-6
24424-99-5
709031-38-9
197142-36-2
7149-65-7
144978-35-8
178172-26-4
194594-23-5
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361442-01-5
197142-36-2
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  • (1S,3S,5S)-3-(Aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester

  • Casno:

    361440-67-7

    (1S,3S,5S)-3-(Aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester

    Min.Order: 1 Gram

    FOB Price:  USD $ 1.0-2.0

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  • (1S,3S,5S)-3-(Aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester

  • Casno:

    361440-67-7

    (1S,3S,5S)-3-(Aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester

    Min.Order: 0

    FOB Price:  USD $ 0.0-0.0

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  • 361440-67-7 cas (1S,3S,5S)-3-(AMinocarbonyl)-2-azabicyclo[3.1.0]he

  • Casno:

    361440-67-7

    361440-67-7 cas (1S,3S,5S)-3-(AMinocarbonyl)-2-azabicyclo[3.1.0]he

    Min.Order: 1 Kilogram

    FOB Price:  USD $ 0.0-0.0

    Packing: According to customer requirements Delivery time: In stock or depands Port of shipment: Ningbo/Shanghai/Qingdao OEM/ODM:Welcome Sample:We can offer our existing samples at once Appearance:white powder/ Refer to COA Storage:Refer to COA

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  • (1S,3S,5S)-3-(Aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester

  • Casno:

    361440-67-7

    (1S,3S,5S)-3-(Aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester

    Min.Order: 1 Kilogram

    FOB Price:  USD $ 1.0-100000.0

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  • (1S,3S,5S)-3-(Aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester

  • Casno:

    361440-67-7

    (1S,3S,5S)-3-(Aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester

    Min.Order: 0 Metric Ton

    FOB Price:  USD $ 0.0-0.0

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  • (1S,3S,5S)-3-(Aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester

  • Casno:

    361440-67-7

    (1S,3S,5S)-3-(Aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester

    Min.Order: 1 Kilogram

    FOB Price:  USD $ 0.0-0.0

    ProName: (1S,3S,5S)-3-(Aminocarbonyl)-2-azabicy... CasNo: 361440-67-7 Molecular Formula: C11H18N2O3 Appearance: white powder Application: Saxagliptin intermediate DeliveryTime: Immediately PackAge: suitable for delivery Port: Qingdao or Shan

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Specification

With the CAS registry number 361440-67-7, The IUPAC name of (1S,3S,5S)-3-(Aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester is tert-Butyl (1R,3S,5S)-3-carbamoyl-2-azabicyclo[3.1.0]hexane-2-carboxylate. In addition, the formula is C11H18N2O3 and the molecular weight is 226.2722.

Physical properties about (1S,3S,5S)-3-(Aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester are: (1)ACD/LogP: -0.534; (2)ACD/LogD (pH 5.5): -0.53; (3)ACD/LogD (pH 7.4): -0.53; (4)ACD/BCF (pH 5.5): 1.00; (5)ACD/BCF (pH 7.4): 1.00; (6)ACD/KOC (pH 5.5): 12.20; (7)ACD/KOC (pH 7.4): 12.20; (8)#H bond acceptors: 5; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 3; (11)Index of Refraction: 1.538; (12)Molar Refractivity: 57.6 cm3; (13)Molar Volume: 184.139 cm3; (14)Polarizability: 22.834 10-24cm3; (15)Surface Tension: 49.5180015563965 dyne/cm; (16)Density: 1.229 g/cm3; (17)Flash Point: 189.024 °C; (18) Enthalpy of Vaporization: 63.821 kJ/mol; (19)Boiling Point: 388.94 °C at 760 mmHg

You can still convert the following datas into molecular structure:
(1)SMILES: CC(C)(C)OC(=O)N1[C@H]2C[C@H]2C[C@H]1C(=O)N
(2)InChI: InChI=1/C11H18N2O3/c1-11(2,3)16-10(15)13-7-4-6(7)5-8(13)9(12)14/h6-8H,4-5H2,1-3H3,(H2,12,14)/t6-,7-,8-/m0/s1
(3)InChIKey: VLAGXRRGXCNITB-FXQIFTODBM

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