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570907

Sigma-Aldrich

Benzyl (S,S,S)-2-azabicyclo[3.3.0]octane-3-carboxylate hydrochloride

97%

Synonym(s):

(S,S,S)-2-Azabicyclo-[3,3,0]-octane carboxylic acid benzylester hydrochloride, (S,S,S)-2-Azabicyclo[3,3,0]octane-3-carboxylic acid benzyl ester hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C15H19NO2 ·HCl
CAS Number:
87269-87-2
Molecular Weight:
281.78
MDL number:
MFCD04974076
UNSPSC Code:
12352005
PubChem Substance ID:
24880599

Assay

97%

optical activity

[α]20/D -26°, c = 1% in DMSO

mp

176-180 °C (lit.)

SMILES string

Cl[H].[H][C@@]12CCC[C@]1([H])N[C@@H](C2)C(=O)OCc3ccccc3

InChI

1S/C15H19NO2.ClH/c17-15(18-10-11-5-2-1-3-6-11)14-9-12-7-4-8-13(12)16-14;/h1-3,5-6,12-14,16H,4,7-10H2;1H/t12-,13-,14-;/m0./s1

InChI key

HLXCXOQXUDRJLF-JKBZPBJLSA-N

Application

Benzyl (S,S,S)-2-azabicyclo[3.3.0]octane-3-carboxylate hydrochloride can be used:
  • In the preparation of ramipril, an angiotensin-converting enzyme (ACE) inhibitor.
  • As a starting material for the synthesis of octahydrocyclopenta[b]pyrrole-2-carbonitrile derivatives as potent DPP4 inhibitors.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

570907-1G:
570907-BULK:
570907-5G:
570907-VAR:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Xun Ji et al.
European journal of medicinal chemistry, 86, 242-256 (2014-08-29)
Based on the previous work in our group and the principle of computer-aided drug design, a series of novel β-amino pyrrole-2-carbonitrile derivatives was designed and synthesized. Compounds 8l and 9l were efficacious and selective DPP4 inhibitors resulting in decreased blood
Expeditious synthesis of Ramipril: an Angiotensin-converting enzyme (ACE) inhibitor
Malakondaiah GC, et al.
Synthetic Communications, 38(11), 1737-1744 (2008)

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