Reacción #641156

Ecuación de reacción

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

triethylamine

→

title compound

Rendimiento 55.8%

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

Rendimiento 55.8%

Disolventes

methylene chloride

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente