858971-57-0

Basic information

• Product Name: (2S,4S)-1-benzyloxycarbonyl-4-methoxy-2-pyrrolidinylmethanol
• Synonyms: (2S,4S)-1-benzyloxycarbonyl-4-methoxy-2-pyrrolidinylmethanol
• CAS NO: 858971-57-0
• Molecular Weight: 265.309
• Mol File: 858971-57-0.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (2S,4S)-1-benzyloxycarbonyl-4-methoxy-2-pyrrolidinylmethanol(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,4S)-1-benzyloxycarbonyl-4-methoxy-2-pyrrolidinylmethanol(858971-57-0)
• EPA Substance Registry System: (2S,4S)-1-benzyloxycarbonyl-4-methoxy-2-pyrrolidinylmethanol(858971-57-0)

Safety Data

• Hazardous Substances Data: 858971-57-0(Hazardous Substances Data)

Upstream product

• 75176-20-4 N-(benzyloxycarbonyl)-cis-4-methoxy-L-proline 
• 74-88-4 methyl iodide 
• 13504-86-4 (2S,4S)-1-benzyloxycarbonyl-4-hydroxyproline 
• 75176-19-1 N-<(phenylmethoxy)carbonyl>-4(S)-methoxy-(S)-proline methyl ester 

Downstream Products

• 858971-58-1 (4S)-methoxy-(2S)-(p-toluenesulfonyloxymethyl)pyrrolidine-1-carboxylic acid benzyl ester 
• 871810-55-8 (2S,4S)-1-benzyloxycarbonyl-4-methoxy-2-trimethylsilyloxymethylpyrrolidine 
• 871810-57-0 trans-4-[1-benzyloxycarbonyl-(4S)-methoxy-(2S)-pyrrolidinylmethoxy]cyclohexanecarboxylic acid ethyl ester 
• 1403562-48-0 C₂₃H₃₃NO₆ 
• 200184-69-6 (2S,4S)-1-benzyloxycarbonyl-4-methoxypyrrolidine-2-carboxyaldehyde 
• 1403562-46-8 (2S,4S)-1-benzyloxycarbonyl-4-methoxy-2-triethylsilyloxymethylpyrrolidine 

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.