2-Chloroacetophenone → (S)-1-(2-oxo-2-phenyl-ethyl)-3-(2-phenyl-2-phenylamino-acetoxy)-1-azonia-bicyclo[2.2.2]octane chloride

Participants

Reaction Steps

To a solution of (S)-quinuclidin-3-yl 2-phenyl-2-(phenylamino)acetate (50.0 mg, 0.15 mmol) in EtOAc (2 mL), is added 2-chloro-1-phenylethanone (23.0 mg, 0.15 mmol) and the reaction is stirred first at RT for 15 hours, then at 70° C. for 7 hours and finally at RT for 3 days. The solvent is removed and the resulting crude is triturated with i-Pr2O/Et2O (3/1) and then with i-Pr2O to achieve the title compound as a beige solid (47.7 mg, 65% yield, chloride salt, mixture of diastereoisomers).

Provenance & Evidence