Potassium peroxymonosulphate → HCID 70654860, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (S)-5-(5-bromo-2-fluoro-phenyl)-5-difluoromethyl-2,5,6,7-tetrahydro-[1,4]thiazepin-3-ylamine (364 mg, 1.03 mmol) in methanol (20 ml) was treated in two portions with potassium peroxymonosulfate (Oxone) (1.27 g, 2.06 mmol) at 23° C. The white suspension was stirred at 23° C. for 5 hours. For the workup, the reaction mixture was quenched at 0° C. under vigorous stirring with water (10 ml), then treated with a diluted solution of sodium hydrogensulfite, a saturated solution of sodium and with dichloromethane. The vigorous stirring was continued for 10 minutes. The organic layer was separated, washed with water, dried over sodium sulfate and evaporated to give a colorless oil. The crude product was purified by chromatography on silica gel using a gradient of dichloromethane and methanol 100:0 to 90:10 as the eluent. The (S)-5-(5-bromo-2-fluoro-phenyl)-5-difluoromethyl-1,1-dioxo-2,5,6,7-tetrahydro-1H-1λ6-[1,4]thiazepin-3-ylamine (322 mg, 81% yield) was obtained as a white solid. MS (ISP): m/z=384.9 [M+H]+and =386.9 [M+2+H]+.

Provenance & Evidence