Potassium Carbonate → (1R*,2R*,5R*)-2-{[3,5-Bis(trifluoromethyl)phenyl]methoxy}-8-(4-chlorobut-2-ynyl)-1-phenyl-8-azabicyclo[3.2.1]octane

Participants

Reaction Conditions

Reaction Steps

A solution of (1R*,2R*,5R*)-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-1-phenyl-8-azabicyclo[3.2.1]octane (Example 60; 400 mg, 0.93 mmol) in dimethylformamide (4 ml) was added to 1,4-dichlorobutyne (0.23 ml, 2.33 mmol) and potassium carbonate (386 mg, 2.79 mmol) in dimethylformamide (2 ml) at 60° C. The reaction mixture was stirred under N2 at 60° C. overnight. The mixture was diluted with water and extracted with ethyl acetate (×3), dried (MgSO4) and concentrated in vacuo to give a brown oil. This was purified by flash column chromatography [2.5%-7.5% methanol in dichloromethane] to give the title compound as a brown oil.

Provenance & Evidence