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

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.

Keywords:

• elimination
• lactam
• peroxide
• pyrrolidin‐2‐one
• rearrangement
• selenoxide

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.