Convenient Synthesis of the Antibiotic Linezolid via an Oxazolidine‐2,4‐dione Intermediate Derived from the Chiral Building Block Isoserine

Abstract

Abstract We describe a new synthesis of the 5‐(aminomethyl)oxazolidin‐3‐one core of linezolid in enantiomerically pure form. The expedient cyclization of the α‐hydroxy amide derived from isoserine and 3‐fluoro‐4‐morpholinoaniline to give the corresponding (aminomethyl)oxazolidine‐2,4‐dione, followed by its mild selective reduction at the C(4)‐position, gave linezolid in almost quantitative overall yield.