Réaction #157859

Équation de réaction

Water

Sodium thiomethoxide

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

→

(5R)-5-{(E)-2-(4-tert-butylphenyl)-2-[6-methoxy-5-(methylsulfanyl)pyridin-2-yl]ethenyl}-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one

Rendement 34.0%

Solvants

N,N-dimethylformamide

Conditions de réaction

Traitement

1. 1
   Extractionfollowed by extraction with ethyl acetate
2. 2
   LavageThe organic layer was washed with water and brine
3. 3
   Séchagedried over anhydrous magnesium sulfate
4. 4
   Filtrationfiltered
5. 5
   Autreafter which the solvent was evaporated under reduced pressure
6. 6
   AutreThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→0:10)

Mode opératoire

Sodium thiomethoxide (44 mg) was added to a solution of (5R)-5-[(E)-2-(5-bromo-6-methoxypyridin-2-yl)-2-(4-tert-butylphenyl)ethenyl]-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one obtained in Reference Example 4-42(1) (150 mg) in N,N-dimethylformamide (1.5 mL), and the mixture was stirred at room temperature for 20 hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate and filtered, after which the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→0:10) to give (5R)-5-{(E)-2-(4-tert-butylphenyl)-2-[6-methoxy-5-(methylsulfanyl)pyridin-2-yl]ethenyl}-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one as a colorless oil (53 mg, 34%).

Source