411232-21-8

Basic information

• Product Name: Cyclopenta[b]pyrrole-2-carboxylic acid, octahydro-, (2S)- (9CI)
• Synonyms: Cyclopenta[b]pyrrole-2-carboxylic acid, octahydro-, (2S)- (9CI)
• CAS NO: 411232-21-8
• Molecular Formula: C8H13NO2
• Molecular Weight: 155.19432
• Product Categories: CARBOXYLICACID;PYRROLE;GLYCINESCAFFOLD
• Mol File: 411232-21-8.mol
• Article Data: 22

Chemical Properties

• Boiling Point: 304.3±25.0 °C(Predicted)
• Appearance: /
• Density: 1.182±0.06 g/cm3(Predicted)
• PKA: 2.47±0.20(Predicted)
• CAS DataBase Reference: Cyclopenta[b]pyrrole-2-carboxylic acid, octahydro-, (2S)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclopenta[b]pyrrole-2-carboxylic acid, octahydro-, (2S)- (9CI)(411232-21-8)
• EPA Substance Registry System: Cyclopenta[b]pyrrole-2-carboxylic acid, octahydro-, (2S)- (9CI)(411232-21-8)

Safety Data

• Hazardous Substances Data: 411232-21-8(Hazardous Substances Data)

Upstream product

• 1030838-82-4 (S)-2-amino-3-(2-oxocyclopentyl)propanoic acid 
• 147406-85-7 (4R,5aR,8aR,9aR)-4-Phenyl-octahydro-cyclopenta[4,5]pyrrolo[2,1-c][1,4]oxazin-1-one 
• 87623-98-1 (2R,3aS,6aR)-1-Acetyl-octahydro-cyclopenta[b]pyrrole-2-carbonitrile 
• 121080-48-6 (S)-Hexahydro-cyclopenta[b]pyrrole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester 
• 156473-27-7 (3aR,6aR)-octahydrocyclopentapyrrole 
• 852547-04-7 benzyl 2-azabicyclo[3.3.0]octane-3-carboxylate 
• 120-92-3 cyclopentanone 
• 59983-35-6 Cyclopentylidene-((S)-2-methoxymethyl-pyrrolidin-1-yl)-amine 
• 765857-50-9 C₈H₁₁NO₂ 
• 147406-85-7 (2R,6R,8S,12S)-1-aza-10-oxo-12-phenyltricyclo<6.4.0^1,8.0^2,6>dodecan-9-one 
• 121080-49-7 benzyl N-benzyloxycarbonyl-(1R,3S,5R)-2-azabicyclo<3.3.0>octane-3-carboxylate 
• 87623-98-1 (2S,3aR,6aR)-1-Acetyl-octahydro-cyclopenta[b]pyrrole-2-carbonitrile 
• 142-29-0 cyclopentene 
• 89226-36-8 N-[(1S,2R)-2-(2-Chloro-2-cyano-ethyl)-cyclopentyl]-acetamide 

Downstream Products

• 109428-53-7 (2S,3aS,6aS)-1-(tert-butoxycarbonyl)octahydrocyclopenta[b]pyrrole-2-carboxylic acid 
• 87333-19-5 Ramipril 
• 1033766-32-3 1-{cyclohexyl-[2-(7-methanesulfonylamino-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-3-yl)acetyl]amino}octahydro-cyclopenta[b]pyrrole-2-carboxylic acid methyl ester 
• 1033766-05-0 N-[3-(4-cyclohexyl-7-hydroxy-5-oxo-2,3,3a,4,5,7a,8,8a-octahydro-1H-3b,4-diaza-cyclopenta[a]inden-6-yl)-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl]methanesulfonamide 
• 1033766-31-2 1-cyclohexylamino-octahydro-cyclopenta[b]pyrrole-2-carboxylic acid methyl ester 
• 1005495-74-8 C₄₃H₆₄N₄O₄ 
• 124002-32-0 (2S,3aS,6aS)-1-[(tert-butoxy)carbonyl]octahydrocyclopenta[b]pyrrole-2-carboxylic acid 
• 1445591-85-4 C₂₁H₂₆BrN₃O₂ 

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.

IMPROVED RAMIPRIL SYNTHESIS

The present invention relates to the preparation of ramipril (formula [1]) from unprotected (2S,3S,6S)-octahydrocyclopenta[b]pyrrole-2-carboxylic acid and to a method for preparing unprotected (2S,3S,6S)-octahydrocyclopenta[b]pyrrole-2- carboxylic acid.