2-Bromo-2'-acetonaphthone → (R)-1-(2-(naphthalen-2-yl)-2-oxoethyl)-3-((R)-2-phenyl-2-(phenylamino)acetoxy)-1-azoniabicyclo[2.2.2]octane bromide

Participants

Reaction Conditions

Reaction Steps

To a solution of (R)—((R)-quinuclidin-3-yl) 2-phenyl-2-(phenylamino)acetate (diastereomer 1 of I2) (75 mg, 0.22 mmol) in acetonitrile (5 ml), was added 2-bromo-1-(naphthalen-2-yl)ethanone (55.5 mg, 0.22 mmol) and the reaction was stirred at 100° C. for 70 minutes under microwave irradiation (UPLC-MS: complete conversion). The solvent was evaporated and the crude was triturated with i-Pr2O-EtOAc (9/1) to obtain (R)-1-(2-(naphthalen-2-yl)-2-oxoethyl)-3-((R)-2-phenyl-2-(phenylamino)acetoxy)-1-azoniabicyclo[2.2.2]octane bromide (121.9 mg, 93% yield).

Provenance & Evidence