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ChemicalBook >> CAS DataBase List >>(1S,3S,5S)-2-(tert-Butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid

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

(1S,3S,5S)-2-(tert-Butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid Structure
(1S,3S,5S)-2-(tert-Butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid structure
CAS No.
197142-36-2
Chemical Name:
(1S,3S,5S)-2-(tert-Butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid
Synonyms
Azabicyclo BOC acid impurity;N-Boc-L-cis-4,5-methanoproline;-2-azabicyclo[3.1.0]hexane-3-carboxylic acid;(1s,3s,5s)-2-boc-2-azabicyclo[3.1.0]hexane-3-carboxylic acid;(1S,3S,5S)-N2-BOC-2-AZABICYCLO[3.1.0]HEXANE-3-CARBOXYLIC ACID;(1S,3S,5S)-2-Boc-2-aza-bicyclo[3.1.0]hexane-3-dicarboxylic acid;(1S,3S,5S)-2-(tert-Butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid;(3S)-2-[(2-methylpropan-2-yl)oxycarbonyl]-2-azabicyclo[3.1.0]hexane-3-carboxylic acid;2-Azabicyclo[3.1.0]hexane-2,3-dicarboxylic acid, 2-(1,1-dimethylethyl) ester, (1S,3S,5S)-;(1S,3S,5S)-2-[(2-methylpropan-2-yl)oxycarbonyl]-2-azabicyclo[3.1.0]hexane-3-carboxylic acid
CBNumber:
CB2825254
Molecular Formula:
C11H17NO4
Molecular Weight:
227.26
MDL Number:
MFCD08691404
MOL File:
Mol file
MSDS File:
SDS
Last updated:2026-09-12 18:51:27
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(1S,3S,5S)-2-(tert-Butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid Properties

Boiling point 355.9±25.0 °C(Predicted)
Density 1.276±0.06 g/cm3(Predicted)
storage temp. 2-8°C
pka 4.03±0.20(Predicted)
Appearance Light yellow to yellow Solid

SAFETY

Risk and Safety Statements

Symbol(GHS)  Exclamation Mark (GHS07)
GHS07
Signal word  Warning
Hazard statements  H302-H315-H319-H335
Precautionary statements  P261-P305+P351+P338

(1S,3S,5S)-2-(tert-Butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid price More Price(49)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Usbiological 412759 (1S,3S,5S)-2-Boc-2-azabicyclo[3.1.0]hexane-3-carboxylic Acid 197142-36-2 10mg $446 2026-06-03 Buy
Usbiological 412759 (1S,3S,5S)-2-Boc-2-azabicyclo[3.1.0]hexane-3-carboxylic Acid 197142-36-2 100mg $2400 2026-06-03 Buy
Biosynth XHA14236 (1S,3S,5S)-2-[(tert-butoxy)carbonyl]-2-azabicyclo[3.1.0]hexane-3-carboxylic acid 197142-36-2 100mg $361 2026-06-05 Buy
Biosynth XHA14236 (1S,3S,5S)-2-[(tert-butoxy)carbonyl]-2-azabicyclo[3.1.0]hexane-3-carboxylic acid 197142-36-2 1g $932.2 2026-06-05 Buy
Matrix Scientific 133494 (1S,3S,5S)-2-(tert-Butoxycarbonyl)-2-azabicyclo-[3.1.0]hexane-3-carboxylic acid 197142-36-2 50.00g $80 2026-05-18 Buy
Product number Packaging Price Buy
412759 10mg $446 Buy
412759 100mg $2400 Buy
XHA14236 100mg $361 Buy
XHA14236 1g $932.2 Buy
133494 50.00g $80 Buy

(1S,3S,5S)-2-(tert-Butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid Chemical Properties, Uses, Production

Uses

(1S,3S,5S)-2-Boc-2-azabicyclo[3.1.0]hexane-3-carboxylic Acid is an impurity of Saxagliptin (S143500), which is a potent and selective reversible inhibitor of dipeptidyl peptidase-4, which is being developed for the treatment of type 2 diabetes. It is absorbed rapidly after oral administration and has a pharmacokinetic profile compatible with once daily dosing.

Synthesis

2-Azabicyclo[3.1.0]hexane-2,3-dicarboxylic acid, 2-(1,1-dimethylethyl) 3-ethyl ester, (1S,3S,5S)-

214193-11-0

(1S,3S,5S)-2-(TERT-BUTOXYCARBONYL)-2-AZABICYCLO[3.1.0]HEXANE-3-CARBOXYLIC ACID

197142-36-2

The general procedure for the synthesis of (1S,3S,5S)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-2,3-dicarboxylic acid using (1S,3S,5S)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid ester as raw material is as follows: the (1S,3S,5S)-2-(tert-butoxycarbonyl)-2-azabicyclo [3.1.0]hexane-3-carboxylic acid (1.4 g) was dissolved in a mixed solvent of methanol (40 mL) and tetrahydrofuran (20 mL), 1N lithium hydroxide solution (10 mL) was added and the reaction was stirred at room temperature overnight. Upon completion of the reaction, the reaction mixture was acidified to pH 4.5 with 2N hydrochloric acid and stirring was continued for 15 min at room temperature. Subsequently, the reaction mixture was extracted with ethyl acetate, the organic phase was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to afford the target product (1S,3S,5S)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid (1.2 g, 96% yield, MNa+ = 250).

References

[1] Patent: WO2006/116157, 2006, A2. Location in patent: Page/Page column 114-115
[2] Patent: EP2272825, 2015, B1. Location in patent: Paragraph 0180; 0181
[3] Angewandte Chemie - International Edition, 2015, vol. 54, # 45, p. 13268 - 13272
[4] Angew. Chem., 2015, # 45, p. 13466 - 13470,4
[5] Patent: CN106928124, 2017, A. Location in patent: Paragraph 0037; 0083-0088

(1S,3S,5S)-2-(tert-Butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid synthesis

178172-26-4
197142-36-2
Synthesis of (1S,3S,5S)-2-(tert-Butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid from (S)-1-Boc-2,3-dihydro-2-pyrrolecarboxylic acid ethyl ester

(1S,3S,5S)-2-(tert-Butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid Preparation Products And Raw materials

Raw materials

2-Azabicyclo[3.1.0]hexane-2,3-dicarboxylic acid, 2-(1,1-dimethylethyl) 3-ethyl ester, (1S,3S,5S)- (S)-1-Boc-2,3-dihydro-2-pyrrolecarboxylic acid ethyl ester (1S,3S,5S)-2-Azabicyclo[3.1.0]hexane-3-carboxylic acid Di-tert-butyl dicarbonate (3S)-3-((tert-butyldiphenylsilyloxy)methyl)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane
Hydrochloric acid Water Methanol Tetrahydrofuran Lithium hydroxide

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Preparation Products

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

(1S,3S,5S)-2-(tert-Butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid Suppliers

Global Suppliers ( 84)
Supplier Tel Email Country ProdList Advantage
PharmaBlock Sciences (Nanjing),Inc. 025-86918202 4000255188 sales@pharmablock.com China 5000 55
Jia Xing Isenchem Co.,Ltd 0573-85285100 18627885956 isenchem@163.com China 9389 66
Syntechem Co.,Ltd info@syntechem.com China 12973 57
T&W GROUP 021-61551611 13296011611 contact@trustwe.com China 9884 58
Shanghai Jian Chao Chemical Technology Co., Ltd. 150-2103-5486 18017383231 983544897@qq.com China 9335 55
Bide Pharmatech Ltd. 400-164-7117 18317119277 product02@bidepharm.com China 40000 60
Suzhou Laing Biological Technology Co., LTD 0512-62968256 18550502935 export@laingbiotec.com China 994 58
Cool Pharm, Ltd 021-60455363 18019463053 sales@coolpharm.com China 8455 58
Nanjing XiZe Biotechnology CO., Ltd. 025-66023220 15250997978 1511893459@qq.com China 4777 55
SanoChem (Chengdu) Tech. Co., Ltd. 28-87999436 02887999436 sales@sano-chem.com China 3792 55
Supplier Advantage
PharmaBlock Sciences (Nanjing),Inc. 55
Jia Xing Isenchem Co.,Ltd 66
Syntechem Co.,Ltd 57
T&W GROUP 58
Shanghai Jian Chao Chemical Technology Co., Ltd. 55
Bide Pharmatech Ltd. 60
Suzhou Laing Biological Technology Co., LTD 58
Cool Pharm, Ltd 58
Nanjing XiZe Biotechnology CO., Ltd. 55
SanoChem (Chengdu) Tech. Co., Ltd. 55

(1S,3S,5S)-2-(tert-Butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid Spectrum

(1S,3S,5S)-2-(TERT-BUTOXYCARBONYL)-2-AZABICYCLO[3.1.0]HEXANE-3-CARBOXYLIC ACID(197142-36-2)1HNMR

197142-36-2 ((1S,3S,5S)-2-(tert-Butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid) Related Search:

Saxagliptin Impurity 15 2-Azabicyclo[3.1.0]hexane-3-carbonitrile, 2-[(2S)-2-aMino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)acetyl]-, (1S,3R,5S)- 1H-Cyclopropa[4,5]pyrrolo[1,2-a]pyrazine-3,6-dione, hexahydro-4-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)-, (1aS,4S,6aR,7aS)- 2-Azabicyclo[3.1.0]hexane-3-carbonitrile, 2-[(2S)-2-aMino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)acetyl]-, (1R,3R,5R)- 2-Azabicyclo[3.1.0]hexane-3-carbonitrile, 2-[(2R)-2-aMino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)acetyl]-, (1S,3S,5S)-
axagliptin Impurity 28 Mesylate Saxagliptin Impurity 16 (1R,3R,5R)-2-Azabicyclo[3.1.0]hexane-3-carboxamide 2,2,2-trifluoroacetate Tricyclo[3.3.1.13,7]decane-1-acetic acid, α-[[(1,1-diMethylethoxy)carbonyl]aMino]-3,5-dihydroxy-, (αS)- (S) - N- Boc- adamantylglycine
2-Azabicyclo[3.1.0]hexane-3-carbonitrile, 2-[(2R)-2-aMino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)acetyl]-, (1R,3S,5R)- 2-Azabicyclo[3.1.0]hexane-3-carbonitrile, 2-[(2R)-2-aMino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)acetyl]-, (1R,3R,5R)- 3H-Cyclopropa[4,5]pyrrolo[1,2-a]pyrazin-3-one, 6-aMino-1,1a,4,6a,7,7a-hexahydro-4-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)-, (1aS,4S,6aR,7aS)- 2-Azabicyclo[3.1.0]hexane-3-carbonitrile, 2-[(2R)-2-aMino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)acetyl]-, (1S,3R,5S)- Saxagliptin Impurity 34
Saxagliptin iMpurity (R)-N-Boc-3-hydroxyadaMantylglycine (1R,3S,5R)-2-Azabicyclo[3.1.0]hexane-3-carboxamide 2,2,2-trifluoroacetic acid

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(1s,3s,5s)-2-boc-2-azabicyclo[3.1.0]hexane-3-carboxylic acid (1S,3S,5S)-N2-BOC-2-AZABICYCLO[3.1.0]HEXANE-3-CARBOXYLIC ACID N-Boc-L-cis-4,5-methanoproline -2-azabicyclo[3.1.0]hexane-3-carboxylic acid (1S,3S,5S)-2-Boc-2-aza-bicyclo[3.1.0]hexane-3-dicarboxylic acid (3S)-2-[(2-methylpropan-2-yl)oxycarbonyl]-2-azabicyclo[3.1.0]hexane-3-carboxylic acid (1S,3S,5S)-2-[(2-methylpropan-2-yl)oxycarbonyl]-2-azabicyclo[3.1.0]hexane-3-carboxylic acid 2-Azabicyclo[3.1.0]hexane-2,3-dicarboxylic acid, 2-(1,1-dimethylethyl) ester, (1S,3S,5S)- Azabicyclo BOC acid impurity (1S,3S,5S)-2-(tert-Butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid 197142-36-2