Reacción #157837

Ecuación de reacción

Water

Tributyltin hydride

azobisisobutyronitrile

O-[1-(6-{(E)-1-(4-tert-butylphenyl)-2-[(2R)-1-(2,4-dimethoxybenzyl)-5-oxopyrrolidin-2-yl]ethenyl}-2-methoxypyridin-3-yl)ethyl] S-methyl carbonodithioate

→

(5R)-5-[(E)-2-(4-tert-butylphenyl)-2-(5-ethyl-6-methoxypyridin-2-yl)ethenyl]-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one

Rendimiento 71.6%

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónfollowed by extraction with chloroform
2. 2
   SecadoThe organic layer was dried over anhydrous magnesium sulfate
3. 3
   Filtraciónfiltered
4. 4
   OtroThe solvent was then evaporated under reduced pressure
5. 5
   OtroThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1)

Procedimiento

Tributyltin hydride (91 μL) and azobisisobutyronitrile (8.5 mg) were added to a solution of O-[1-(6-{(E)-1-(4-tert-butylphenyl)-2-[(2R)-1-(2,4-dimethoxybenzyl)-5-oxopyrrolidin-2-yl]ethenyl}-2-methoxypyridin-3-yl)ethyl] S-methyl carbonodithioate (109 mg) in toluene (2 mL), and the mixture was stirred at 120° C. for 30 minutes. Water was added to the reaction solution, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1) to give (5R)-5-[(E)-2-(4-tert-butylphenyl)-2-(5-ethyl-6-methoxypyridin-2-yl)ethenyl]-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one as a colorless oil (65 mg).

Fuente