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

Participants

Reaction Steps

22.1 g (100 mmol) of (4S,5S)-4-benzyl-oxazolidin-2-one-5-carboxylic acid were dissolved in 120 ml of ethanol. 1.2 ml of concentrated sulphuric acid(11 mmol) were added and the mixture refluxed for 2 hours. 90 ml of ethanolwere then removed by distillation. This solution was then added dropwise within 30 minutes to a suspension of 5.3 g (140 mmol) of NaBH4 in 40 ml of ethanol. Once addition was complete, stirring was continued for 3 hours. 100 ml of water were cautiously added to the colourless suspension and a pH value of 7 was established with concentrated HCl. After 2 hours' stirring at room temperature, the temperature was reduced to 0° C. for a further 2 hours. The solid was filtered out and washed with a littleiced water. The product was then dried under a vacuum at 45° C.

Provenance & Evidence