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

Participants

Reaction Conditions

Reaction Steps

A methylene chloride solution (6 ml) of dimethyl sulfoxide (2.0 ml, 28.2 mmol) was added dropwise to a methylene chloride solution (30 ml) of oxalyl chloride (1.7 ml, 19.5 mmol) at −60° C. over a period of 10 minutes and stirred at −60° C. for another 10 minutes. Then, a methylene chloride solution (140 ml) of tert-butyl 4-hydroxycyclohexylcarbamate (2.56 g, 11.9 mmol) was added dropwise thereto over a period of 35 minutes, and the resulting mixture was stirred at −60° C. for 40 minutes. After triethylamine (8.4 ml, 60.3 mmol) was added thereto at −60° C., the resulting mixture was warmed up to room temperature spontaneously. Water was added to the reaction mixture, followed by extraction with chloroform. The organic layer was washed with a saturated aqueous ammonium chloride solution and a saturated aqueous sodium chloride solution and then dried over magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: chloroform/ethyl acetate) to obtain tert-butyl 4-oxocyclohexylcarbamate (2.23 g, 87%).

Provenance & Evidence