871810-57-0

Upstream product

• 13504-86-4 (2S,4S)-1-benzyloxycarbonyl-4-hydroxyproline 
• 75176-19-1 N-<(phenylmethoxy)carbonyl>-4(S)-methoxy-(S)-proline methyl ester 
• 3618-04-0 trans-4-hydroxy-cyclohexane carboxylic acid ethyl ester 
• 1403562-46-8 (2S,4S)-1-benzyloxycarbonyl-4-methoxy-2-triethylsilyloxymethylpyrrolidine 
• 17159-79-4 ethyl 4-oxocyclohexane-1-carboxylate 
• 871810-55-8 (2S,4S)-1-benzyloxycarbonyl-4-methoxy-2-trimethylsilyloxymethylpyrrolidine 
• 858971-57-0 (2S,4S)-1-benzyloxycarbonyl-4-methoxy-2-pyrrolidinylmethanol 
• 200184-69-6 (2S,4S)-1-benzyloxycarbonyl-4-methoxypyrrolidine-2-carboxyaldehyde 
• 1403562-47-9 trans-ethyl 4-[(triethylsilyl)oxy]cyclohexane-1-carboxylate 

Relevant academic research and scientific papers

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.