Reaction #164214

Reaction equation

(R)-((R)-quinuclidin-3-yl) 3-phenyl-2-(phenylamino)propanoate

2-bromo-1-phenylethanone

→

title compound

Yield 98.1%

(R)-1-(2-oxo-2-phenylethyl)-3-((R)-3-phenyl-2-(phenylamino)propanoyloxy)-1-azoniabicyclo[2.2.2]octane bromide

Yield 98.1%

Conditions

Workup

1. 1
   Otherthe mixture reacted in a closed vessel under MW irradiation for 1 hour at 100° C. (LC-MS monitoring: complete conversion)
2. 2
   OtherSolvent is removed under reduced pressure and residue
3. 3
   Otheris triturated with EtOAc

Procedure

To a solution of (R)-((R)-quinuclidin-3-yl) 3-phenyl-2-(phenylamino)propanoate (Diastereoisomer 1 of C22) (50.0 mg, 0.14 mmol), is added 2-bromo-1-phenylethanone (28.4 mg, 0.14 mmol) and the mixture reacted in a closed vessel under MW irradiation for 1 hour at 100° C. (LC-MS monitoring: complete conversion). Solvent is removed under reduced pressure and residue is triturated with EtOAc to obtain the title compound as a white solid (75.5 mg, 98% yield, bromide salt, single diastereoisomer).

Source