반응 #545931

반응 방정식

4-hydroxy-1-t-butoxycarbonylpiperidine

sodium hydride

(2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-phenylacetic acid

carbonyldiimidazole

→

title compound

수율 55.1%

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

수율 55.1%

용매

ethyl acetate

dimethylformamide

반응 조건

후처리

1. 1
   workup.WAITfollowed by another 30 minutes
2. 2
   workup.STIRRING' stirring
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
   기타the residue obtained
8. 8
   기타was purified on silica gel column chromatography (eluent: hexane/ethyl acetate=3/1)

실험 절차

To a solution of 128 mg of (2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-phenylacetic acid in 3 ml of dimethylformamide, 81 mg of carbonyldiimidazole was added and stirred for 30 minutes. Then 121 mg of 4-hydroxy-1-t-butoxycarbonylpiperidine and 10 mg of sodium hydride were added successively, followed by another 30 minutes' stirring. 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 obtained was purified on silica gel column chromatography (eluent: hexane/ethyl acetate=3/1) to provide 121 mg of the title compound.

출처