Water → (2S,4R)-N-methanesulfonyl-4-hydroxy-2-hydroxymethylpyrrolidine

Participants

Reaction Steps

To 360 ml of tetrahydrofuran was added 3.98 g (0.105 mol) of lithium aluminum hydride, and the mixture was stirred. To this mixture was slowly added dropwise a solution of 16.6 g (0.07 mol) of (2S,4R)-N-methanesulfonyl-4-hydroxyproline ethyl ester [III] in 200 ml of tetrahydrofuran under agitation and ice-cooling. After stirring the suspension at 0° C. for 3 hours and then at room temperature for 3 hours, 14 ml of water was added dropwise in small portions to the suspension under ice-cooling, and thereafter the mixture was stirred for 30 minutes. Any insoluble matter was removed by filtration and the filtrate was concentrated until dryness under reduced pressure whereby 11.9 g (yield: 87%) of an oily substance was obtained.

Provenance & Evidence