Trifluoroacetic acid → HCID 86586710, compound

Participants

Reaction Steps

A mixture of (1R*,2R*,5S*,6S*)-8-benzyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-6-(tert-butoxycarbonyl)-1-phenyl-8-azabicyclo[3.2.1]octane (Description 22; 250 mg, 0.4 mmol), trifluoroacetic acid (0.8 ml) and dichloromethane (1.2 ml) was stirred at room temperature overnight and concentrated in vacuo. The residue was treated with semicarbazide hydrochloride (355 mg, 3.2 mmol), triethylamine (1 ml, 7.2 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (457 mg, 4.2 mmol), and 4-N,N-dimethylaminopyridine (35 mg, 0.28 mmol). The mixture was stirred at room temperature over weekend, quenched with saturated aqueous NaHCO3 and extracted into dichloromethane. The combined organic extracts were dried (Na2SO4) and concentrated. The residue was purified by chromatography on silica gel (dichloromethane:methanol:ammonia) to give the title compound (278 mg, 55%).

Provenance & Evidence