Reacción #157829

Ecuación de reacción

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

sodium bicarbonate

→

(5R)-5-[(E)-2-(5-amino-6-methoxypyridin-2-yl)-2-(4-tert-butylphenyl)ethenyl]pyrrolidin-2-one

Rendimiento 44.0%

Disolventes

trifluoroacetic acid

anisole

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónfollowed by extraction with ethyl acetate
2. 2
   LavadoThe organic layer was washed with brine
3. 3
   Secadodried over anhydrous magnesium sulfate
4. 4
   Otroafter which the solvent was evaporated under reduced pressure
5. 5
   OtroThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1→1:4)

Procedimiento

A solution of (5R)-5-[(E)-2-(5-amino-6-methoxypyridin-2-yl)-2-(4-tert-butylphenyl)ethenyl]-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one (198 mg) in trifluoroacetic acid (4 mL) and anisole (2 mL) was stirred at 80° C. for six hours. Saturated aqueous sodium bicarbonate was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate, after which the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1→1:4) to give (5R)-5-[(E)-2-(5-amino-6-methoxypyridin-2-yl)-2-(4-tert-butylphenyl)ethenyl]pyrrolidin-2-one as a light brown solid (61 mg, 44%).

Fuente