Phenacyl bromide → (3R)-1-(2-oxo-2-phenylethyl)-3-(2-phenyl-2-(vinyloxycarbonylamino)-acetoxy)-1-azoniabicyclo[2.2.2]octane bromide

Participants

Reaction Steps

To a solution of (R)-quinuclidin-3-yl 2-phenyl-2-(vinyloxycarbonylamino)acetate (C32) (70.0 mg, 0.21 mmol) in EtOAc (2 ml) and acetonitrile (0.5 ml), was added 2-bromo-1-phenylethanone (46.4 mg, 0.23 mmol). The reaction was stirred at RT for 15 hours, and then the solvent was evaporated. The resulting solid was triturated with i-Pr2O/EtOAc (1/1) to obtain (3R)-1-(2-oxo-2-phenylethyl)-3-(2-phenyl-2-(vinyloxycarbonylamino)-acetoxy)-1-azoniabicyclo[2.2.2]octane bromide (82.4 mg; 73% yield).

Provenance & Evidence