Dimethyl Sulfoxide → tert-butyl N-(4-oxocyclohexyl)carbamate

Participants

Reaction Conditions

Reaction Steps

To a solution of oxalyl chloride (2.33 mL, 26.7 mmol) in methylene chloride (50 mL) cooled at −60° C. was added a solution of DMSO (4 mL, 56 mmol) in methylene chloride (5 mL) followed by a solution of trans-4-tert-butoxycarbonylaminocyclohexanol (5 g, 23 mmol) obtained above in methylene chloride (20 mL). After stirring at −60° C. for 20 minutes, triethylamine (16.1 mL, 116 mmol) was added. The mixture was allowed to warm to room temperature and stirring was continued for 30 minutes. Water was added. The organic phase was separated and the aqueous layer was extracted with methylene chloride twice. The combined organic phase was washed with brine, dried over MgSO4 and concentrated. Flash chromatography eluting with a gradient of 3% to 5% to 10% MeOH/CH2Cl2 provided 4.5 g (90%) of the title compound. MS (M+H)+214. Found 236 (M+Na)+.

Provenance & Evidence