4-Fluoro-2-hydroxyphenacyl bromide → (R)-1-(2-(4-fluoro-2-hydroxyphenyl)-2-oxoethyl)-3-((R)-2-phenyl-2-(phenylamino)acetoxy)-1-azoniabicyclo[2.2.2]octane bromide

Participants

Reaction Steps

To a solution of (R)—((R)-quinuclidin-3-yl) 2-phenyl-2-(phenylamino)acetate (diastereomer 1 of I2) (100 mg, 0.30 mmol) in EtOAc (3 ml) and acetonitrile (2 ml), was added 2-bromo-1-(4-fluoro-2-hydroxyphenyl)ethanone (69.3 mg, 0.30 mmol), and the reaction was stirred at room temperature for 15 hours (UPLC-MS: complete conversion). The solvent was evaporated and the crude was triturated in i-Pr2O-EtOAc (1/1) to obtain (R)-1-(2-(4-fluoro-2-hydroxyphenyl)-2-oxoethyl)-3-((R)-2-phenyl-2-(phenylamino)acetoxy)-1-azoniabicyclo[2.2.2]octane bromide (154.0 mg, 91% yield).

Provenance & Evidence