Water → (1R*,2R*,5R*)-8-Benzyl-2-(3,5-bis(trifluoromethyl)benzoyl)-1-(4-fluorophenyl)-8-azabicyclo[3.2.1]octane

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Reaction Steps

(1R*,2 R*,5R*)-8-Benzyl-1-(4-fluorophenyl)-8-azabicyclo[3.2.1]octan-2-ol (Description 15; 1.23 g, 3.95 mmol), and triethylamine (0.61 ml, 4.35 mmol) in dichloromethane were stirred with 4-dimethylaminopyridine (5 crystals) and 3,5-bis(trifluoromethyl)benzoyl chloride at room temperature for a weekend. The reaction mixture was poured into water and extracted with dichloromethane (×3), dried (MgSO4) and concentrated in vacuo to give a yellow oil. This was purified by flash column chromatography [10%-20% ethyl acetate in iso-hexane] to give the title compound as a yellow solid (1.27 g, 58%).

Provenance & Evidence