4-Fluorophenethyl bromide → (R)-3-((bis(3-fluorophenyl)-methoxy)carbonylamino)-1-(4-fluorophenethyl)-1-azoniabicyclo[2.2.2]octane bromide

Participants

Reaction Steps

(R)-bis(3-Fluorophenyl)methyl quinuclidin-3-ylcarbamate (55 mg, 0.14 mmol, prepared as in example 1) was dissolved in ethyl acetate (2 ml), and 1-(2-bromoethyl)-4-fluorobenzene (21 μl, 0.15 mmol) was added. The reaction was stirred at room temperature for 24 hours, then 1-(2-bromoethyl)-4-fluorobenzene (6.21 μl, 0.04 mmol) was added again. After being stirred at room temperature for 2 days, the reaction was concentrated under vacuum, and the crude was first purified by flash chromatography (DCM/MeOH=9/1) and then triturated with DCM/Et2O (1/1) to obtain (R)-3-((bis(3-fluorophenyl)-methoxy)carbonylamino)-1-(4-fluorophenethyl)-1-azoniabicyclo[2.2.2]octane bromide (45 mg).

Provenance & Evidence