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

Participants

Reaction Steps

A solution 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; 2.7 mmol) was treated with ammonia solution in dioxane (0.5M, 10 ml, 5 mmol), triethylamine (0.6 ml, 4.3 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (960 mg, 5.02 mmol), and 4-N,N-dimethylaminopyridine (120 mg, 1 mmol). The mixture was stirred for 24 hours, diluted with ethyl acetate (100 ml), washed with 10% aqueous citric acid, saturated aqueous NaHCO3, dried (Na2SO4) and concentrated. The residue was purified by chromatography on silica gel (iso-hexane:ethyl acetate) to give the title compound (850 mg, 56%).

Provenance & Evidence