Réaction #44615

Équation de réaction

methylene chloride

(E)-3-[(2R,5S)-1-(3-butenoyl)-5-(3,4,5-trifluorophenyl)pyrrolidin-2-yl]acrylic acid ethyl ester

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title compound

Rendement 70.3%

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

Rendement 70.3%

Solvants

triethylamine

Conditions de réaction

Traitement

1. 1
   Températureunder reflux for 2 hr
2. 2
   Concentrationconcentrated under reduced pressure
3. 3
   AutreThe residue was purified by silica gel column chromatography (heptane:ethyl acetate=1:1 to 0:1)

Mode opératoire

A methylene chloride solution (60 mL) of (E)-3-[(2R,5S)-1-(3-butenoyl)-5-(3,4,5-trifluorophenyl)pyrrolidin-2-yl]acrylic acid ethyl ester (1.33 g) and Grubbs catalyst second generation (153 mg) was heated under reflux for 2 hr. The reaction solution was allowed to cool to room temperature, and then triethylamine (0.5 mL) was added thereto. The resulting mixture was stirred for 1 hr and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (heptane:ethyl acetate=1:1 to 0:1) to give 680 mg of the title compound. The physical property values of this compound were as follows:

Source