Benzyl Bromide → HCID 69430665, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 60% NaH (66 mg, 1.64 mmol) in DMF (3 ml) was added a solution of ([3RS,4RS]-4-hydroxymethyl-1-methanesulfonyl-pyrrolidin-3-yl)-methanol (327 mg, 1.56 mmol) in DMF (5 ml) at −12° C. After 5 min, benzylbromide (286 mg, 1.64 mmol) was added and the mixture was stirred at −12° C. for 30 min. The mixture was allowed to warm to room temperature. The solvent was evaporated. Water was added and extracted with dichloromethane. The organic phase was dried, filtered and evaporated. Flash chromatography (hexane/EtOAc 2:1=>1:1) gave 275 mg (58%) of ([3RS,4RS]-4-benzyloxymethyl-1-methanesulfonyl-pyrrolidin-3-yl)-methanol as a colorless oil, MS: 358 (M+OAc)−.

Provenance & Evidence