Synthesis 2006(5): 875-879  
DOI: 10.1055/s-2006-926318
PAPER
© Georg Thieme Verlag Stuttgart · New York

Towards Simplifying the Chemistry of N-Acyliminium Ions: A One-Pot Protocol for the Preparation of 5-Acetoxy Pyrrolidin-2-ones and 2-Acetoxy N-Alkoxycarbonyl Pyrrolidines from Imides

Fridrich Szemes Jr., Anthony Fousse, Raja Ben Othman, Till Bousquet, Mohamed Othman, Vincent Dalla*
Unité de Recherche en Chimie Organique et Macromoléculaire, Faculté des Sciences et Techniques de l’Université du Havre, 25 rue Philippe Lebon, BP 540, 76058 Le Havre CEDEX, France
Fax: +33(2)32744391; e-Mail: vincent.dalla@univ-lehavre.fr;
Further Information

Publication History

Received 24 August 2005
Publication Date:
07 February 2006 (online)

Abstract

A new one-step protocol for the synthesis of acetoxy lactams starting from imides has been developed. This method involves regiospecific reduction of the imide with LiEt3BH, then capture of the transient lithium alkoxide by acetic anhydride.

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18

Compounds 5d and 5e were prepared from (S)- and (R)-pyroglutamic acid using typical procedures for functional-group transformations similar to those employed for 5a-c.

19

The yield of 2b fell to 63% when 5 g of 1b was used (the corresponding hydroxy lactam was also isolated in 16% yield) and to 40% when the reaction was carried out on a 7.5 g scale.