2-Bromo-1-(thiophen-3-yl)ethan-1-one → (R)-3-(2-(benzo[b]thiophen-3-yl)-2-(phenylamino)acetoxy)-1-(2-oxo-2-(thiophen-3-yl)ethyl)-1-azoniabicyclo[2.2.2]octane bromide

Participants

Reaction Steps

2-Bromo-1-(thiophen-3-yl)ethanone (52.2 mg, 0.25 mmol) was added portion-wise to a solution of (R)-quinuclidin-3-yl 2-(benzo[b]thiophen-3-yl)-2-(phenylamino)acetate (C19) (100 mg, 0.25 mmol) in EtOAc (2 ml). The reaction was stirred at room temperature for 3 hours. The precipitate was filtered, washed with EtOAc and purified by preparative HPLC (Eluent: CH3CN, H2O) to obtain (R)-3-(2-(benzo[b]thiophen-3-yl)-2-(phenylamino)acetoxy)-1-(2-oxo-2-(thiophen-3-yl)ethyl)-1-azoniabicyclo[2.2.2]octane bromide (32 mg, 21.0% yield).

Provenance & Evidence