반응 #545943

반응 방정식

t-butyl 4-((2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-(4-bromophenyl)ethanoyloxy)-tetrahydropyridine-1(2H)-carboxylate

vinyl tri-n-butyltin

→

title compound

t-butyl 4-((2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-(4-vinylphenyl)ethanoyloxy)tetrahydropyridine-1(2H)-carboxylate

용매

dioxane

반응 조건

후처리

1. 1
   온도' heating
2. 2
   workup.DISTILLATIONDistilling the solvent off under reduced pressure
3. 3
   workup.ADDITIONthe resulting residue was diluted with ethyl acetate
4. 4
   세척washed successively with water and saturated brine
5. 5
   건조dried over anhydrous sodium sulfate
6. 6
   workup.DISTILLATIONDistilling the solvent off under reduced pressure
7. 7
   기타the residue was purified on silica gel column chromatography (eluent: hexane/ethyl acetate=4/1)

실험 절차

To a solution of 125 mg of the t-butyl 4-((2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-(4-bromophenyl)ethanoyloxy)-tetrahydropyridine-1(2H)-carboxylate as obtained in Referential Example 52 in 4 ml of dioxane, 0.10 ml of vinyl tri-n-butyltin and 20 mg of tetrakistriphenylpalladium were added at room temperature, followed by 24 hours' heating under reflux at 110° C. in nitrogen atmosphere. Distilling the solvent off under reduced pressure, the resulting residue was diluted with ethyl acetate, washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. Distilling the solvent off under reduced pressure, the residue was purified on silica gel column chromatography (eluent: hexane/ethyl acetate=4/1) to provide 90 mg of the title compound.

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