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

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:2026-05-28 00:45:57

Product description	Number	Pack Size	Price
(1S,3S,5S)-2-Boc-2-azabicyclo[3.1.0]hexane-3-carboxylic Acid	412759	10mg	$446
(1S,3S,5S)-2-Boc-2-azabicyclo[3.1.0]hexane-3-carboxylic Acid	412759	100mg	$2400
(1S,3S,5S)-2-[(tert-butoxy)carbonyl]-2-azabicyclo[3.1.0]hexane-3-carboxylic acid	XHA14236	100mg	$361
(1S,3S,5S)-2-[(tert-butoxy)carbonyl]-2-azabicyclo[3.1.0]hexane-3-carboxylic acid	XHA14236	1g	$932.2
(1S,3S,5S)-2-(tert-Butoxycarbonyl)-2-azabicyclo-[3.1.0]hexane-3-carboxylic acid	133494	50.00g	$80
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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)	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(61)

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

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( 74)Suppliers

Supplier	Tel	Email	Country	ProdList	Advantage
Nanjing ChemLin Chemical Industry Co., Ltd.	025-83697070	product@chemlin.com.cn	CHINA	3009	60
Alchem Pharmtech,Inc.	8485655694	sales@alchempharmtech.com	United States	63687	58
NINGBOBENKANGJS PHARMTECHCO., LTD	+8615990591583 15990591583		CHINA	2029	58
Labnetwork lnc.	+86-27-50766799 +8618062016861	contact@labnetwork.com	China	19987	58
sgtlifesciences pvt ltd	+8617013299288	dj@sgtlifesciences.com	China	12373	58
Suzhou Laing Biotechnology Co.,Ltd	+86-13004516015 +86-18149392822	christina@laingbiotec.com	China	777	58
Protheragen-ING	+16313385890	info@protheragen-ing.com	United States	3868	58
HANGZHOU LEAP CHEM CO., LTD.	+86-571-87711850	market18@leapchem.com	China	43333	58
Aladdin Scientific		tp@aladdinsci.com	United States	57505	58
Suzhou ARTK Medchem Co., Ltd.	+8618118463618	sales1@artkmedchem.com	China	39021	58

Supplier	Advantage
Nanjing ChemLin Chemical Industry Co., Ltd.	60
Alchem Pharmtech,Inc.	58
NINGBOBENKANGJS PHARMTECHCO., LTD	58
Labnetwork lnc.	58
sgtlifesciences pvt ltd	58
Suzhou Laing Biotechnology Co.,Ltd	58
Protheragen-ING	58
HANGZHOU LEAP CHEM CO., LTD.	58
Aladdin Scientific	58
Suzhou ARTK Medchem Co., Ltd.	58

(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)- Saxagliptin Impurity 16 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)-

(1R,3S,5R)-2-AZABICYCLO[3.1.0]HEXANE-3-CARBOXAMIDE 2,2,2-TRIFLUOROACETIC ACID 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)- (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 axagliptin Impurity 28 Mesylate

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(1S,3S,5S)-2-(TERT-BUTOXYCARBONYL)-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 N-Boc-L-cis-4,5-methanoproline -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 (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-Boc-2-aza-bicyclo[3.1.0]hexane-3-dicarboxylic acid 197142-36-2

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