tert-Butanol → tert-Butyl (1-methylcyclopropyl)carbamate

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-methylcyclopropanecarboxylic acid (3.52 g) in tert-butanol (50 mL) were added diphenylphosphoryl azide (7.58 mL) and triethylamine (4.90 mL), and the mixture was stirred at 80° C. for 15 hours. After cooling to room temperature, the reaction mixture was concentrated in vacuo. To the residue were added water and an aqueous saturated sodium hydrogencarbonate solution, and the mixture was extracted with diethylether. The organic layer was dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo, and the resultant crude product was purified by column chromatography on silica gel (solvent: hexane/ethyl acetate=90/10 to 87/13) to give 1-methyl-1-[N-(tert-butoxycarbonyl)amino]-cyclopropane (4.66 g, yield: 77%) as a colorless solid.

Provenance & Evidence