Chemoenzymatic synthesis of (3 S,4 S)- and (3 R,4 R)-3-methoxy-4-methylaminopyrrolidine

Ahmed Kamal; Ahmad Ali Shaik; Mahendra Sandbhor; M. Shaheer Malik; Harumi Kaga

doi:10.1016/j.tetlet.2004.08.167

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Chemoenzymatic synthesis of (3 S,4 S)- and (3 R,4 R)-3-methoxy-4-methylaminopyrrolidine

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Chemoenzymatic synthesis of (3 S,4 S)- and (3 R,4 R)-3-methoxy-4-methylaminopyrrolidine

Ahmed Kamal, Ahmad Ali Shaik, Mahendra Sandbhor, M. Shaheer Malik and Harumi Kaga

Tetrahedron letters, Vol.45(43), pp.8057-8059

18/10/2004

DOI: https://doi.org/10.1016/j.tetlet.2004.08.167

Abstract

[Display omitted] Facile chemoenzymatic enantioselective synthesis of (3 S,4 S)-3-methoxy-4-methylaminopyrrolidine, a key intermediate for a new quinolone antitumor compound AG-7352 has been described. This methodology illustrates the preparation of 3-azido-1-benzyloxycarbonyl-4-hydroxypyrrolidine starting from diallylamine via 1-benzyloxycarbonyl-3-pyrroline obtained by ring-closing metathesis (RCM) employing Grubbs’ catalyst. Enzymatic transesterification employing PS-C lipase gave (3 S,4 S)-3-azido-1-benzyloxycarbonyl-4-hydroxypyrrolidine in >99% ee, which upon methylation of the hydroxyl group followed by sequential reactions gave the desired intermediates, (3 S,4 S)-1- tert-butoxycarbonyl-3- tert-butoxycarbonylamino-4-methoxypyrrolidine.

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Title: Chemoenzymatic synthesis of (3 S,4 S)- and (3 R,4 R)-3-methoxy-4-methylaminopyrrolidine
Creators - without role: Ahmed Kamal - Indian Institute of Chemical Technology
Ahmad Ali Shaik - Indian Institute of Chemical Technology
Mahendra Sandbhor - Indian Institute of Chemical Technology
M. Shaheer Malik - Biotransformation Laboratory, Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500 007, India
Harumi Kaga - National Institute of Advanced Industrial Science and Technology
Publication Details: Tetrahedron letters, Vol.45(43), pp.8057-8059
Publisher: Elsevier Ltd
Identifiers: 9931398008331
Academic Unit: Umm Al Qura University
Language: English
Resource Type: Journal article