tert-Butyl Carbonate as a Nucleophile in Epoxide Ring Opening: A Cascade Synthesis of 5-(Hydroxymethyl)oxazolidin-2-one

Abstract

We report an efficient and scalable synthesis of 5-(hydroxymethyl)oxazolidin-2-ones using tert-butyl carbonate as a nucleophile in a Boc₂O-mediated epoxide ring-opening cascade. Optimization identified Et₃N as key to high yields, with electron-withdrawing aryl groups further enhancing efficiency (up to 91%). Mechanistic studies support the nucleophilic role of tert-butyl carbonate. This versatile method enables access to pharmaceutically relevant compounds, including intermediates for Linezolid, highlighting its value in medicinal chemistry.