2-Bromo-1-(1,3-thiazol-2-yl)ethan-1-one → (3R)-1-(2-oxo-2-(thiazol-2-yl)ethyl)-3-(2-phenyl-2-(piperidin-1-yl)acetoxy)-1-azoniabicyclo[2.2.2]octane bromide

Participants

Reaction Steps

(R)-Quinuclidin-3-yl 2-phenyl-2-(piperidin-1-yl)acetate (120 mg, 0.36 mmol) was dissolved in ethyl acetate (3.65 ml) and 2-bromo-1-(thiazol-2-yl)ethanone (83 mg, 0.42 mmol) was added. The mixture was stirred at room temperature for 16 hours. The solvent was evaporated and the residue was purified by flash chromatography (DCM/MeOH=95/5 to 9/1) to obtain (3R)-1-(2-oxo-2-(thiazol-2-yl)ethyl)-3-(2-phenyl-2-(piperidin-1-yl)acetoxy)-1-azoniabicyclo[2.2.2]octane bromide (125 mg, 0.234 mmol, 64.0% yield) pale brown solid.

Provenance & Evidence