Acetyl bromide → HCID 86660312, compound

Participants

Reaction Steps

Acetyl bromide (10 μl, 0.14 mmol) was added to a solution of (R)-1-(2-(4-hydroxyphenyl)-2-oxoethyl)-3-((R)-2-phenyl-2-(phenylamino)acetoxy)-1-azoniabicyclo[2.2.2]octane bromide (diastereomer 1 of I71) (70 mg, 0.13 mmol) in TEA (19.5 μl, 0.14 mmol) and DCM (3 ml). The reaction mixture was stirred at room temperature overnight. The solvent was evaporated, and the crude product was purified first by trituration with Et2O, then by flash-chromatography (DCM/MeOH=95/5) and finally by preparative HPLC (eluents: CH3CN/H2O) to obtain (R)-1-(2-(4-acetoxyphenyl)-2-oxoethyl)-3-((R)-2-phenyl-2-(phenylamino)acetoxy)-1-azoniabicyclo[2.2.2]octane bromide (24 mg, 31.9% yield).

Provenance & Evidence