4-(Chloromethyl)-2-phenyl-1,3-oxazole → (3R)-3-(2-phenyl-2-(piperidin-1-yl)acetoxy)-1-((2-phenyloxazol-4-yl)methyl)-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 4-(chloromethyl)-2-phenyloxazole (70.7 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 (3R)-3-(2-phenyl-2-(piperidin-1-yl)acetoxy)-1-((2-phenyloxazol-4-yl)methyl)-1-azoniabicyclo[2.2.2]octane chloride (55 mg, 34.6% yield) as an off-white solid.

Provenance & Evidence