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

Participants

Reaction Steps

To a solution of (R)—((R)-quinuclidin-3-yl) 2-(benzyloxy-carbonylamino)-2-phenylacetate (40 mg, 0.10 mmol) in EtOAc (3 ml), 2-bromo-1-phenylethanone (22.2 mg, 0.11 mmol) was added and the reaction was stirred at RT for 15 hours, and then the solvent was evaporated. The crude was purified by silica gel flash chromatography (DCM/MeOH=93/7) to obtain (R)-3-((R)-2-(benzyloxycarbonylamino)-2-phenylacetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane bromide (45.0 mg; 74.8% yield).

Provenance & Evidence