Reacción #43314

Ecuación de reacción

Cyclopentanone

methanol

4-benzyloxy-1-{4-[(3S)-3-pyrrolidinyloxy]phenyl}-1H-pyridin-2-one

→

title compound

Rendimiento 53.0%

4-benzyloxy-1-(4-{[(3S)-1-cyclopentyl-3-pyrrolidinyl]-oxy}phenyl)-1H-pyridin-2-one

Rendimiento 53.0%

Disolventes

Ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.WAITsired at room temperature for an hour
2. 2
   Lavadowas then washed with saturated aqueous sodium bicarbonate solution and saturated brine
3. 3
   Secadodried over anhydrous potassium carbonate
4. 4
   ConcentraciónThe solvent was concentrated under reduced pressure
5. 5
   Otrothe resulting residue was purified on silica gel chromatography (C-300; methanol:chloroform=1:10)

Procedimiento

Cyclopentanone (0.017 mL, 0.186 mmol) and a 0.3 mol Zn[B(CN)H3]2 methanol solution (0.4 mL, 0.12 mmol, prepared from ZnCl2 and NaB(CN)H3) were added to a methanol solution (1 mL) of 4-benzyloxy-1-{4-[(3S)-3-pyrrolidinyloxy]phenyl}-1H-pyridin-2-one (45 mg, 0.124 mmol) and sired at room temperature for an hour. Ethyl acetate was added to the reaction liquid, which was then washed with saturated aqueous sodium bicarbonate solution and saturated brine, and dried over anhydrous potassium carbonate. The solvent was concentrated under reduced pressure and the resulting residue was purified on silica gel chromatography (C-300; methanol:chloroform=1:10) to provide the title compound (28.2 mg, 53%).

Fuente