반응 #545945

반응 방정식

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

sodium sulfite

→

title compound

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

용매

ethyl acetate

tetrahydrofuran water

ethyl acetate

반응 조건

후처리

1. 1
   workup.WAITfollowed by an hour
2. 2
   workup.STIRRINGstirring
3. 3
   기타The reaction liquid
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
   workup.DISSOLUTIONthe residue was dissolved in 1 ml of methanol
8. 8
   workup.ADDITIONTo the solution 10 mg of sodium borohydride was added
9. 9
   workup.STIRRINGstirred for 10 minutes
10. 10
    workup.ADDITIONacetone was added
11. 11
    기타The reaction liquid
12. 12
    세척washed successively with water and saturated brine
13. 13
    건조dried over anhydrous sodium sulfate
14. 14
    workup.DISTILLATIONDistilling the solvent off under reduced pressure
15. 15
    기타the resulting residue was purified on preparative thin layer chromatography (Kieselgel™ 60F254, Art 5744 (Merck), hexane/ethyl acetate=1/1)

실험 절차

To a solution of 69 mg of the t-butyl 4-((2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-(4-vinylphenyl)ethanoyloxy)-tetrahydropyridine-1(2H)-carboxylate as obtained in Referential Example 56 in 2 ml of tetrahydrofuran-water (1:1), 85 mg of sodium periodide and 0.1 ml of 2% osmium tetraoxide were added at 0° C., followed by an hour's stirring at the same temperature. Adding sodium sulfite to the reaction liquid, stirring was continued for further 30 minutes. The reaction liquid 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 dissolved in 1 ml of methanol. To the solution 10 mg of sodium borohydride was added, stirred for 10 minutes and acetone was added. The reaction liquid 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 resulting residue was purified on preparative thin layer chromatography (Kieselgel™ 60F254, Art 5744 (Merck), hexane/ethyl acetate=1/1) to provide 42 mg of the title compound as a colorless oily substance.

출처