Réaction #157838

Équation de réaction

hydrobromic acid

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

Water

→

6-{(E)-1-(4-tert-butylphenyl)-2-[(2R)-1-(2,4-dimethoxybenzyl)-5-oxopyrrolidin-2-yl]ethenyl}-3-ethylpyridin-2(1H)-one

Rendement 85.3%

Solvants

1,4-dioxane

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 resulting residue was purified by silica gel column chromatography (chloroform:methanol=10:0→3:1)

Mode opératoire

48% hydrobromic acid (0.6 mL) was added to a solution of (5R)-5-[(E)-2-(4-tert-butylphenyl)-2-(5-ethyl-6-methoxypyridin-2-yl)ethenyl]-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one (59 mg) in 1,4-dioxane (0.6 mL), and the mixture was stirred at 65° C. for 1.5 hours. Water 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 resulting residue was purified by silica gel column chromatography (chloroform:methanol=10:0→3:1) to give 6-{(E)-1-(4-tert-butylphenyl)-2-[(2R)-1-(2,4-dimethoxybenzyl)-5-oxopyrrolidin-2-yl]ethenyl}-3-ethylpyridin-2(1H)-one as a colorless oil (49 mg).

Source