Réaction #157725

Équation de réaction

(5R)-1-(2,4-Dimethoxybenzyl)-5-ethynylpyrrolidin-2-one

4-tert-butyliodobenzene

water

→

(5R)-5-[(4-tert-butylphenyl)ethynyl]-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one

Rendement 84.0%

Solvants

triethylamine

Conditions de réaction

Traitement

1. 1
   workup.WAITover one hour
2. 2
   workup.STIRRINGthe mixture was stirred at room temperature for three hours
3. 3
   Extractionfollowed by extraction with ethyl acetate
4. 4
   LavageThe organic layer was washed with brine
5. 5
   Séchagedried over anhydrous magnesium sulfate
6. 6
   Filtrationfiltered
7. 7
   AutreThe solvent was then evaporated under reduced pressure
8. 8
   AutreThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:0→1:1)

Mode opératoire

Copper iodide (74 mg) and bis(triphenylphosphine)palladium(II) dichloride (135 mg) were added to a solution of 4-tert-butyliodobenzene (3.0 g) in triethylamine (10 mL), and the mixture was stirred at room temperature for 15 minutes. (5R)-1-(2,4-Dimethoxybenzyl)-5-ethynylpyrrolidin-2-one (1.0 g) was added thereto over one hour, and the mixture was stirred at room temperature for three hours. The reaction solution was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with brine, 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=1:0→1:1) to give (5R)-5-[(4-tert-butylphenyl)ethynyl]-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one as a colorless powder (1.25 g, 84%).

Source