4-Toluenesulfonyl chloride → tert-Butyl N-[1-({[(4-methylbenzene)sulfonyl]oxy}methyl)cyclopropyl]carbamate

Participants

Reaction Steps

To a solution of tert-butyl 1-(hydroxymethyl)cyclopropylcarbamate (290 g, 1.55 mol) in DCM (2900 mL) was added DMAP (227 g, 1.86 mol) followed by 4-methylbenzene-1-sulfonyl chloride (323 g, 1.69 mol) in several batches at 10° C. After 2 hours, the reaction mixture was washed with water (2×1000 mL), dried over sodium sulfate, and concentrated under reduced pressure to afford {1-[(tert-butoxycarbonyl)amino]cyclopropyl}methyl 4-methylbenzenesulfonate. The material was used without further purification.

Provenance & Evidence