Hydrochloric Acid → (4S,5S)-5-hydroxymethyl-4-phenylmethyloxazolidinone

Participants

Reaction Conditions

Reaction Steps

A solution of 50 g of a 97.2:2.8 mixture of the (4S,5S):(4S,5R) isomers of 4-benzyl-2-oxo-oxazolidine-5-carboxylic acid in 300 ml of methanol was combined with 1 ml of sulphuric acid and refluxed for 3.5 hours. The solution was cooled to 0° C. and adjusted to pH 7 with a solution of 30% sodium methoxide in methanol. 10.26 g of sodium borohydride were added to the solution at 0°-3° C. After 1 hour's stirring at 0° C., the suspension is adjusted to pH 1 at 0°-20° C. with 25% hydrochloric acid. After the addition of water and stirring at -10° C., the suspension is filtered. 41.5 g (89%) of 99% (4S,5S)-4-benzyl-5-hydroxymethyl-oxazolidin-2-one, melting point 168°-171° C., [α]D20 : -79.1° (1% in methanol), were obtained.

Provenance & Evidence