Phenacyl bromide → (R)-3-[2-(4-fluoro-benzylamino)-2-phenyl-acetoxy]-1-(2-oxo-2-phenyl-ethyl)-1-azonia-bicyclo[2.2.2]octane bromide

Participants

Reaction Steps

A mixture of (R)-quinuclidin-3-yl 2-(4-fluorobenzylamino)-2-phenylacetate (C78) (61 mg, 0.17 mmol) and 2-bromo-1-phenylethanone (33.0 mg, 0.17 mmol) in ethyl acetate (3 mL) is stirred at RT overnight. The solid is collected by suction filtration and washed with Et2O. The product is further purified by flash chromatography (DCM/MeOH=95/5 to 92/8) to obtain the title compound as a white solid (35 mg, 37% yield, bromide salt, mixture of diastereoisomers).

Provenance & Evidence