Phenacyl bromide → (3R)-3-(2-(methoxycarbonylamino)-2-phenylacetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane bromide

Participants

Reaction Steps

To a solution of (R)-quinuclidin-3-yl 2-(methoxycarbonylamino)-2-phenylacetate (C26) (58.0 mg, 0.18 mmol) in EtOAc (3 ml) and CH3CN (1 ml), was added 2-bromo-1-phenylethanone (39.9 mg, 0.20 mmol). The reaction was stirred at RT for 15 hours, and then the solvent was evaporated. The crude was purified by flash chromatography (DCM/MeOH=95/5 to 92/8) and the resulting product was triturated with i-Pr2O to obtain (3R)-3-(2-(methoxycarbonylamino)-2-phenylacetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane bromide (55.2 mg; 58.6% yield).

Provenance & Evidence