62851-29-0

Basic information

• Product Name: 2,2-Pyrrolidinedicarboxylic acid, 1-(4-chlorophenyl)-5-oxo-3-phenyl-, diethyl ester
• CAS NO: 62851-29-0
• Molecular Formula: C22H22ClNO5
• Molecular Weight: 415.873
• Mol File: 62851-29-0.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 2,2-Pyrrolidinedicarboxylic acid, 1-(4-chlorophenyl)-5-oxo-3-phenyl-, diethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-Pyrrolidinedicarboxylic acid, 1-(4-chlorophenyl)-5-oxo-3-phenyl-, diethyl ester(62851-29-0)
• EPA Substance Registry System: 2,2-Pyrrolidinedicarboxylic acid, 1-(4-chlorophenyl)-5-oxo-3-phenyl-, diethyl ester(62851-29-0)

Safety Data

• Hazardous Substances Data: 62851-29-0(Hazardous Substances Data)

Upstream product

• 5203-01-0 diethyl 2-[(4-chlorophenyl)amino]malonate 
• 102-92-1 cinnamoyl chloride 
• 102-92-1 Cinnamoyl chloride 

Downstream Products

• 1307780-27-3 diethyl 1-(4-chlorophenyl)-5-thioxo-3-phenyl-pyrrolidine-2,2-dicarboxylate 
• 34241-33-3 (2S,3S)-1-(4-Chloro-phenyl)-5-oxo-3-phenyl-pyrrolidine-2-carboxylic acid 
• 87430-08-8 3-(4-Chloro-phenyl)-3,3a,5,9b-tetrahydro-1H-benzo[e]indole-2,4-dione 
• 613686-83-2 1-(4-chlorophenyl)-2,2-dicarbethoxy-3-phenylpyrrolidine 
• 87430-02-2 1-(4-Chloro-phenyl)-5-oxo-3-phenyl-pyrrolidine-2,2-dicarboxylic acid 

Relevant articles and documents

Chemoselective reduction of a lactam carbonyl group in the presence of a gem-dicarboxylate by sodium borohydride and iodine: A facile entry to N-aryl trisubstituted pyrroles

Several N-aryl γ-lactam gem dicarboxylates were chemoselectively reduced to cyclic amine diesters by using sodium borohydride-iodine system. The reduction in all cases was completed within 2.5 h after refluxing in THF. The cyclic amine products were isolated after aqueous (acidic) workup in good yields. Hydrolytic decarboxylation followed by dehydrogenation produced N-aryl carboethoxy pyrroles.

A convenient synthesis of tricyclic gamma-lactams, stimulating B-C-D rings of azasteroids via Michael addition reaction

Cinnamoylchloride on treatment with arylaminomalonates produced the γ-lactam diester derivatives. Highly stereoselective hydrolysis of the diester, produced the trans acid, which on homologation by Arndt-Eistert's method followed by PPA cyclization generated the tricyclic γ-lactam derivatives simulating B-C-D ring of many azasteroids in good overall yield.