Acetyl chloride → (1R*,2R*,5S*,6R*)-8-Allyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-6-(methoxycarbonyl)-1-phenyl-8-azabicyclo[3.2.1]octane

Participants

Reaction Steps

Acetyl chloride (5 ml) was cautiously added to methanol (25 ml) and (1R*,2R*,5S*,6R*)-8-allyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-6-(tert-butoxycarbonyl)-1-phenyl-8-azabicyclo[3.2.1]octane (Example 94; 1.23 g, 2.16 mmol) dissolved in the resulting solution. After standing for 4 weeks, the solvent was removed under reduced pressure and the residue partitioned between ethyl acetate (25 ml) and saturated aqueous sodium carbonate (2×15 ml), the organic layers dried (MgSO4) and evaporated to leave the title compound as a gum. (1.07 g, 94%).

Provenance & Evidence