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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 37, 2007 - Issue 5
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Original Articles

N‐Benzyl‐5‐hydroxy‐3‐pyrrolidin‐2‐one by Hydrogen Peroxide Oxidation of N‐Benzyl‐3‐phenylseleno‐2‐pyrrolidinone

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Pages 813-819 | Received 26 Jul 2006, Published online: 10 Mar 2007
 

Abstract

Using the known peroxide oxidation of N‐benzyl‐3‐phenylseleno‐2‐pyrrolidinone with 30% hydrogen peroxide at −5°C after 3.5 h, we prepared the expected N‐benzyl‐3‐pyrrolin‐2‐one. However, reaction with 30% hydrogen peroxide for 12 h (−5°C→ambient) gave the unexpected product N‐benzyl‐5‐hydroxy‐3‐pyrrolidin‐2‐one in 84% isolated yield. This procedure is a new synthetic route to N‐benzyl‐5‐hydroxy‐3‐pyrrolidin‐2‐one.

Acknowledgment

We thank the R&C Patterson Trust for partial funding of this work. We thank Martha Morton, coordinator of the NMR facility, and Marvin Thompson, coordinator of the mass spectrometer facility, for their generous help in this work.

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