tert-Butanol → HCID 72213060, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of crude 1-(2-bromo-pyridin-4-yl)-cyclopropanecarboxylic acid (0.350 g, 1.45 mmol) in tert-butanol (7 mL) in a pressure vessel is added diphenylphosphoryl azide (0.312 mL, 1.45 mmol) and triethylamine (0.202 mL, 1.45 mmol). The tube is sealed and the reaction mixture is stirred at 90° C. After 4 hours, the pressure vessel is cooled in an ice-bath, vented and opened. The reaction mixture is concentrated in vacuo. The resulting residue is dissolved in ethyl acetate (70 mL), washed with saturated aqueous ammonium chloride (70 mL) and saturated aqueous sodium bicarbonate (70 mL), dried over MgSO4, filtered and concentrated. The residue is purified by silica gel chromatography eluting with a gradient of 0-50% ethyl acetate in heptane to afford [1-(2-bromo-pyridin-4-yl)-cyclopropyl]-carbamic acid tert-butyl ester.

Provenance & Evidence