Triethylamine → (1R*,2R,5S*,6R*)-8-Benzyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-1-phenyl-8-azabicyclo[3.2.1]octan-6-carbohydrazide

Participants

Reaction Steps

A mixture of (1R*,2R*,5S*,6R*)-8-benzyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-1-phenyl-8-azabicyclo[3.2.1]octan-6-carboxylic acid trifluoroacetate (Example 53; 1.6 g, 2.35 mmol), triethylamine (1 ml, 7.1 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (910 mg, 4.7 mmol), 4-N,N-dimethylaminopyridine (20 mg, 0.16 mmol), dichloromethane (15 ml) and hydrazine (1M solution in THF, 5 ml, 5 mmol) was stirred at room temperature over the weekend. The reaction mixture was diluted with ethyl acetate and washed with saturated aqueous NaHCO , water and brine. The organic layer was dried (Na2SO4) and concentrated. The residue was purified by chromatography on silica gel (dichloromethane:methanol) to give the title compound (1 g, 74%).

Provenance & Evidence