2-Bromo-4'-nitroacetophenone → HCID 86660313, compound

Participants

Reaction Steps

2-Bromo-1-(4-nitrophenyl)ethanone (290 mg, 1.19 mmol) was added to a solution of (R)—((R)-quinuclidin-3-yl) 2-phenyl-2-(phenylamino)acetate (diastereomer 1 of I2) (400 mg, 1.19 mmol) in EtOAc (15 ml). The reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into a Parr's vial and diluted with MeOH. Pd/C (cat amount; about 10 mg) was added, and reaction is hydrogenated at 35 pound per square inch (psi) for 8 hours (UPLC-MS: complete conversion). The catalyst was removed by filtration, and the clear solution was concentrated under vacuum. The residue was triturated with Et2O and filtered to obtain (R)-1-(2-(4-aminophenyl)-2-oxoethyl)-3-((R)-2-phenyl-2-(phenylamino)acetoxy)-1-azoniabicyclo[2.2.2]octane bromide (632 mg, 97% yield).

Provenance & Evidence