tert-Butanol → HCID 67002375, compound

Participants

Reaction Steps

To a solution of 1-cyclopropanecarbonyl-cyclopentane carboxylic acid (0.36 g, 2.0 mmol) in t-BuOH (10 mL) was added triethylamine (0.33 mL, 2.4 mmol) followed by diphenylphosphoryl azide (0.47 mL, 2.2 mmol). The reaction mixture was stirred at reflux for 6 h then cooled to room temperature and poured into saturated aqueous NaHCO3. The aqueous layer was extracted with EtOAc (3×). The combined organics were dried over Na2SO4 and concentrated. The residue was purified by chromatography on 24 g SiO2 (0% to 30% EtOAc/hexanes) to afford 63 mg (13%) of (1-cyclopropanecarbonyl-cyclopentyl)-carbamic acid tert-butyl ester as a white solid.

Provenance & Evidence