2-chloro-N-(1,2-oxazol-3-yl)acetamide → (3R)-1-(2-(isoxazol-3-ylamino)-2-oxoethyl)-3-(2-phenyl-2-(piperidin-1-yl)acetoxy)-1-azoniabicyclo[2.2.2]octane chloride

Participants

Reaction Steps

To a solution of (R)-quinuclidin-3-yl 2-phenyl-2-(piperidin-1-yl)acetate (100 mg, 0.30 mmol) in EtOAc (2 ml) and acetonitrile (1 ml), was added 2-chloro-N-(isoxazol-3-yl)acetamide (58.7 mg, 0.36 mmol). The reaction was stirred at room temperature for 30 hours and then the solvents were evaporated. Purification by flash chromatography (DCM/MeOH=9/1) followed by trituration with Et2O afforded the title compound (55 mg, 36.9% yield) as an off-white solid.

Provenance & Evidence