Реакция #641156

Уравнение реакции

ethyl (E)-3-[(2R,5S)-1-(3-butenoyl)-5-(2,4,6-trifluorophenyl)pyrrolidin-2-yl]acrylate

triethylamine

→

title compound

Выход 55.8%

(3S,8aR)-3-(2,4,6-trifluorophenyl)-2,3,6,8a-tetrahydro-1H-indolizin-5-one

Выход 55.8%

Растворители

methylene chloride

Условия реакции

Обработка

1. 1
   Температураunder reflux for two hours
2. 2
   workup.WAITThe reaction solution was left
3. 3
   КонцентрированиеThe reaction solution was concentrated under reduced pressure
4. 4
   Другоеthe residue was purified by silica gel column chromatography (heptane->heptane:ethyl acetate=1:1->ethyl acetate)

Методика

A solution of ethyl (E)-3-[(2R,5S)-1-(3-butenoyl)-5-(2,4,6-trifluorophenyl)pyrrolidin-2-yl]acrylate (1.35 g) and Grubbs catalyst 2nd generation (155 mg) in methylene chloride (70 mL) was heated under reflux for two hours. The reaction solution was left to cool to room temperature. Then, triethylamine (0.5 mL) was added to the reaction solution, and the mixture was stirred for one hour. The reaction solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (heptane->heptane:ethyl acetate=1:1->ethyl acetate) to obtain 548 mg of the title compound. The property value of the compound is as follows.

Источник