Hydrochloric Acid → HCID 178521150, compound

Participants

Reaction Steps

2-Chloro-1-phenylethanone (29.3 mg, 0.12 mmol) was added to a solution of (R)-quinuclidin-3-yl 2-(6-(benzyloxy)pyridin-3-yl)-2-(phenylamino)acetate (C53) (84 mg, 0.19 mmol, mixture of diastereomers) in EtOAc (4 ml). The reaction was stirred at room temperature overnight, and then a catalytic amount of 10% Pd/C (about 10 mg) and 37% HCl (0.50 ml) were added, and the reaction was hydrogenated at 20 psi for 2 hours. Pd/C is removed by filtration, and the clear solution was evaporated to dryness. The crude was purified by preparative HPLC to obtain (3R)-3-(2-(6-hydroxypyridin-3-yl)-2-(phenylamino)acetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane chloride (20.3 mg, 18% yield).

Provenance & Evidence