Issue 1, 2009

A new entry into cis-3-amino-2-methylpyrrolidines viaring expansion of 2-(2-hydroxyethyl)-3-methylaziridines

Abstract

3-Amino-2-methylpyrrolidines were prepared via a novel protocol, involving the reductive ring closure and O-deprotection of γ-acetoxy-α-chloroketimines towards 2-(2-hydroxyethyl)-3-methylaziridines, followed by ring expansion of the latter into 3-bromopyrrolidines via intermediate bicyclic aziridinium salts and consecutive nucleophilic displacement of the bromo atom by azide towards 3-azidopyrrolidines. A final reduction of the azide moiety furnished 3-amino-2-methylpyrrolidines in high yields. Thus, a new formal synthesis of the antipsychotic emonapride was developed through preparation and further aroylation of cis-3-amino-1-benzyl-2-methylpyrrolidine.

Graphical abstract: A new entry into cis-3-amino-2-methylpyrrolidines viaring expansion of 2-(2-hydroxyethyl)-3-methylaziridines

Supplementary files

Article information

Article type
Paper
Submitted
22 Sep 2008
Accepted
10 Oct 2008
First published
06 Nov 2008

Org. Biomol. Chem., 2009,7, 135-141

A new entry into cis-3-amino-2-methylpyrrolidines viaring expansion of 2-(2-hydroxyethyl)-3-methylaziridines

M. D'hooghe, W. Aelterman and N. De Kimpe, Org. Biomol. Chem., 2009, 7, 135 DOI: 10.1039/B816617J

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