109428-53-7

Basic information

• Product Name: 2-Azabicyclo[3.3.0]octane-3-carboxylic acid
• Synonyms: 2-azabicyclo[3.3.0]octane-3-carboxylic acid;Cyclopenta[b]pyrrole-2-carboxylic acid, octahydro-, (2S,3aS,6aS)- (9CI);EOS-61473
• CAS NO: 109428-53-7
• Molecular Formula: C₈H₁₃NO₂
• Molecular Weight: 155.19
• Product Categories: CARBOXYLICACID;PYRROLE
• Mol File: 109428-53-7.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 304.333 °C at 760 mmHg
• Flash Point: 137.856 °C
• Appearance: /
• Density: 1.183 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.518
• CAS DataBase Reference: 2-Azabicyclo[3.3.0]octane-3-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Azabicyclo[3.3.0]octane-3-carboxylic acid(109428-53-7)
• EPA Substance Registry System: 2-Azabicyclo[3.3.0]octane-3-carboxylic acid(109428-53-7)

Safety Data

• Hazardous Substances Data: 109428-53-7(Hazardous Substances Data)

Usage

General Description

2-Azabicyclo[3.3.0]octane-3-carboxylic acid, also known as quinuclidine-3-carboxylic acid, is a chemical compound with a bicyclic structure and a carboxylic acid functional group. It is a heterocyclic compound containing a nitrogen atom in the bicyclic ring system. 2-Azabicyclo[3.3.0]octane-3-carboxylic acid has potential applications in the pharmaceutical industry as a building block for the synthesis of various drugs, particularly in the development of muscarinic receptor antagonists. Its unique structure and properties make it a valuable intermediate in organic synthesis for the production of pharmaceuticals and other complex molecules. Additionally, it is used in research and development to study the biological activity and pharmacological effects of compounds containing quinuclidine-3-carboxylic acid.

InChI:InChI=1/C8H13NO2/c10-8(11)7-4-5-2-1-3-6(5)9-7/h5-7,9H,1-4H2,(H,10,11)

Upstream product

• 93779-31-8 benzyl (1S,3S,5S)-2-azabicyclo<3.3.0>octane-3-carboxylate 
• 121154-37-8 benzyl N-benzyloxycarbonyl-(1S,3S,5S)-2-azabicyclo<3.3.0>octane-3-carboxylate 
• 765857-50-9 C₈H₁₁NO₂ 
• 1296306-77-8 2-aza-bicyclo[3.3.0]octane-3-carboxylic acid 
• 94569-19-4 2-aza-bicyclo[3.3.0]octane-3-carboxylic acid benzyl ester hydrochloride 
• 1296242-98-2 C₁₅H₁₇NO₂ 
• 59983-35-6 Cyclopentylidene-((S)-2-methoxymethyl-pyrrolidin-1-yl)-amine 
• 120-92-3 cyclopentanone 
• 142-29-0 cyclopentene 
• 89226-36-8 N-[(1S,2R)-2-(2-Chloro-2-cyano-ethyl)-cyclopentyl]-acetamide 
• 87623-98-1 (2R,3aS,6aR)-1-Acetyl-octahydro-cyclopenta[b]pyrrole-2-carbonitrile 
• 87269-87-2 benzyl (2S,3AS,6AS)-octahydrocyclopenta[b]pyrrole-2-carboxylate hydrochloride 
• 1030838-82-4 (S)-2-amino-3-(2-oxocyclopentyl)propanoic acid 
• 87269-86-1 (S,S,S)-2-azabicyclo<3.3.0>octane-3-carboxylic acid hydrochloride 

Downstream Products

• 87269-87-2 benzyl (2S,3AS,6AS)-octahydrocyclopenta[b]pyrrole-2-carboxylate hydrochloride 
• 124002-32-0 (2S,3aS,6aS)-1-[(tert-butoxy)carbonyl]octahydrocyclopenta[b]pyrrole-2-carboxylic acid 
• 1005495-74-8 C₄₃H₆₄N₄O₄ 
• 87333-19-5 Ramipril 
• 1445591-85-4 C₂₁H₂₆BrN₃O₂ 
• 852546-84-0 (2S,3aS,6aS)-benzyl octahydrocyclopenta[b]pyrrole-2-carboxylate 4-toluenesulfonate (1:1) 
• 93779-31-8 benzyl (1R^*,3R^*,5R^*)-2-azabicyclo<3.3.0>octane-3-carboxylate 
• 133616-95-2 (1S,5S,3'R)-2-Carbamoyl-(3'-methylphenyl)-2-azabicyclo<3.3.0>octan 
• 133616-97-4 (1S,5S)-2-(1-Cyclohexen-1-yl)-2-azabicyclo<3.3.0>octan 
• 125419-12-7 methyl N-methyl-(1SR,3SR,5SR)-2-azabicyclo<3.3.0>octane-3-carboxylate 

Relevant articles and documents

Continuous Flow Synthesis of ACE Inhibitors From N-Substituted l-Alanine Derivatives

A strategy for the continuous flow synthesis of angiotensin converting enzyme (ACE) inhibitors is described. An optimization effort guided by in situ IR analysis resulted in a general amide coupling approach facilitated by N-carboxyanhydride (NCA) activation that was further characterized by reaction kinetics analysis in batch. The three-step continuous process was demonstrated by synthesizing 8 different ACE inhibitors in up to 88 % yield with throughputs in the range of ≈0.5 g h?1, all while avoiding both isolation of reactive intermediates and process intensive reaction conditions. The process was further developed by preparing enalapril, a World Health Organization (WHO) essential medicine, in an industrially relevant flow platform that scaled throughput to ≈1 g h?1.

METHOD FOR THE SYNTHESIS OF A RAMIPRIL INTERMEDIATE

The present invention relates to a process for the preparation of octahydrocyclopenta[b]pyrrole-2-carboxylic acid and esters thereof of general formula (1) in the presence of a cobalt and/or nickel comprising catalyst and to the use of compounds of general formula (1) in the synthesis of ramipril.

NOVEL CARBAMOYLGLYCINE DERIVATIVES

The present invention relates to carbamoylglycine derivatives, a process for the preparation of carbamoylglycine derivatives and the use of carbamoylglycine derivatives in the preparation of enantiomerically enriched α-amino acids. Furthermore, the present invention relates to the preparation of pharmaceutically active products such as perindopril and ramipril using the novel carbamoylglycine derivatives.