200184-69-6

Basic information

• Product Name: (2S,4S)-1-benzyloxycarbonyl-4-methoxypyrrolidine-2-carboxyaldehyde
• Synonyms: (2S,4S)-1-benzyloxycarbonyl-4-methoxypyrrolidine-2-carboxyaldehyde
• CAS NO: 200184-69-6
• Molecular Weight: 263.293
• Mol File: 200184-69-6.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (2S,4S)-1-benzyloxycarbonyl-4-methoxypyrrolidine-2-carboxyaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,4S)-1-benzyloxycarbonyl-4-methoxypyrrolidine-2-carboxyaldehyde(200184-69-6)
• EPA Substance Registry System: (2S,4S)-1-benzyloxycarbonyl-4-methoxypyrrolidine-2-carboxyaldehyde(200184-69-6)

Safety Data

• Hazardous Substances Data: 200184-69-6(Hazardous Substances Data)

Upstream product

• 858971-57-0 (2S,4S)-1-benzyloxycarbonyl-4-methoxy-2-pyrrolidinylmethanol 
• 75176-19-1 N-<(phenylmethoxy)carbonyl>-4(S)-methoxy-(S)-proline methyl ester 
• 13504-86-4 (2S,4S)-1-benzyloxycarbonyl-4-hydroxyproline 

Downstream Products

• 871810-57-0 trans-4-[1-benzyloxycarbonyl-(4S)-methoxy-(2S)-pyrrolidinylmethoxy]cyclohexanecarboxylic acid ethyl ester 

Relevant articles and documents

A concise synthesis of a very late antigen-4 antagonist trans-4-[1-[[2,5-dichloro-4-(1-methyl-3-indolylcarboxyamide)phenyl]acetyl]-(4S) -methoxy-(2S)-pyrrolidinylmethoxy]cyclohexanecarboxylic acid via reductive etherification

This contribution describes a concise synthesis to ethyl trans-[(4S)-methoxy-(25)-pyrrolidinylmethoxy] cyclohexanecarboxylate (2b) as a key intermediate of very late antigen-4 (VLA-4) antagonist trans-4-[1-[[2,5- dichloro-4-(1-methyl-3-indolylcarboxyamide)phenyl]acetyl]-(4S)-methoxy-(2S) -pyrrolidinylmethoxy] cyclohexanecarboxylic acid (1). The synthesis employs a reductive etherification as a key reaction using (2S,4S)-1-benzyloxycarbonyl-4- methoxypyrrolidine-2-carboxyaldehyde (12) and trans-4- triethylsilyloxycyclohexanecarboxilic acid ethyl ester (13b). This synthesis provides 2b in 6 steps with 38% overall yield from commercially available starting material.