Réaction #157829

Équation de réaction

(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

Rendement 44.0%

Solvants

trifluoroacetic acid

anisole

Conditions de réaction

Traitement

1. 1
   Extractionfollowed by extraction with ethyl acetate
2. 2
   LavageThe organic layer was washed with brine
3. 3
   Séchagedried over anhydrous magnesium sulfate
4. 4
   Autreafter which the solvent was evaporated under reduced pressure
5. 5
   AutreThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1→1:4)

Mode opératoire

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%).

Source