tert-Butanol → Tert-butyl (1-(4-chlorophenyl)cyclopropyl)carbamate

Participants

Reaction Conditions

Reaction Steps

A solution of 1-(4-chlorophenyl)cyclopropanecarboxylic acid (10.5 g, 53.3 mmol) in toluene (70 mL) was treated successively with triethylamine (15 mL, 106.6 mmol), diphenylphosphorylazide (DPPA) (12.7 mL, 58.6 mmol) and tert-butanol (25 mL, 267 mmol). The reaction mixture was stirred at 80° C. for 20 hours. The mixture was partitioned between ethyl acetate (300 mL) and water (100 mL). The phases were separated and the organic phase was washed with water (80 mL) then brine (100 mL). The organic phase was dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by flash chromatography (SiO2, 10% ethyl acetate in hexanes). The tert-butyl (1-(4-chlorophenyl)cyclopropyl)carbamate was obtained as a white solid (14 g). LCMS [M+H]: 268.

Provenance & Evidence