반응 #9335

반응 방정식

NH4Cl

L-selectride

10-3

[4-((1R,2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-{4-[(tert-butyl-dimethyl-silanyloxy)-cyclohexyl-methyl]-phenyl}-5-oxo-cyclopentyl)-but-2-ynyloxy]-acetic acid methyl ester

H2O2

→

alcohol

수율 61.9%

[4-((1R,2S,3R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-{4-[(tert-butyl-dimethyl-silanyloxy)-cyclohexyl-methyl]-phenyl}-5-hydroxy-cyclopentyl)-but-2-ynyloxy]-acetic acid methyl ester

수율 61.9%

용매

THF

반응 조건

후처리

1. 1
   workup.STIRRINGThe resulting mixture was stirred at room temperature for 45 min.
2. 2
   추출The resulting mixture was extracted with ethyl acetate (3×40 mL)
3. 3
   세척the combined ethyl acetate solution was washed with brine
4. 4
   건조The solution was then dried (Na2SO4)
5. 5
   여과filtered
6. 6
   기타evaporated
7. 7
   기타Purification by flash chromatography on silica gel (25% ethyl acetate/hexanes)

실험 절차

L-selectride (0.76 mL, 0.76 mmol, 1 M/THF) was added to a −78° C. THF (20 mL) solution of 10-3 (415 mg, 0.63 mmol). The reaction was stirred for 1 h and then 3% H2O2 (14 mL) was added. The resulting mixture was stirred at room temperature for 45 min. and then saturated NH4Cl solution (60 mL) was added. The resulting mixture was extracted with ethyl acetate (3×40 mL) and the combined ethyl acetate solution was washed with brine. The solution was then dried (Na2SO4), filtered and evaporated. Purification by flash chromatography on silica gel (25% ethyl acetate/hexanes) gave the title alcohol (255 mg, 0.39 mmol, 61%).

출처