Dimethyl Sulfoxide → Tert-butyl 3-oxopyrrolidine-1-carboxylate

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Reaction Conditions

Reaction Steps

A flask was charged with a solution of oxalyl chloride (3.2 ml, 33 mmol) in dichloromethane (60 ml). The solution was cooled to −60° C., and a solution of dimethylsulfoxide (5.1 ml, 66 mmol) in dichloromethane (10 ml) was added dropwise, such that the internal temperature was maintained at −60° C. This was followed by the dropwise addition of a solution of tert-butyl 3-hydroxypyrrolidine-1-carboxylate (5.6 g, 30 mmol) in dichloromethane (25 ml). The resulting solution was allowed to stir for 1 hour −60° C., then triethyamine (21 ml) was added and the mixture was allowed to warm to room temperature. The solution was diluted with 150 ml of water and extracted with dichloromethane (2×150 ml). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated to afford tert-butyl 3-oxopyrrolidine-1-carboxylate as a white solid.

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