2-Chloroacetophenone → (3R)-3-(2-(benzo[b]thiophen-7-yl)-2-(phenylamino)acetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane chloride

Participants

Reaction Steps

2-Chloro-1-phenylethanone (35.4 mg, 0.23 mmol) was added to a solution of (R)-quinuclidin-3-yl 2-(benzo[b]thiophen-7-yl)-2-(phenylamino)acetate (C27) (90 mg, 0.23 mmol) in EtOAc (3 ml). The reaction was stirred at room temperature overnight. The solvent was removed under vacuum and the crude was triturated with Et2O. The compound was purified by preparative HPLC (Eluent: CH3CN/H2O) to obtain (3R)-3-(2-(benzo[b]thiophen-7-yl)-2-(phenylamino)acetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane chloride (26.6 mg, 21.2% yield).

Provenance & Evidence