反応 #9335

反応方程式

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

収率 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

収率 61.9%

溶媒

THF

反応条件

後処理

1. 1
   workup.STIRRINGThe resulting mixture was stirred at room temperature for 45 min.
2. 2
   抽出The resulting mixture was extracted with ethyl acetate (3×40 mL)
3. 3
   洗浄the combined ethyl acetate solution was washed with brine
4. 4
   乾燥The solution was then dried (Na2SO4)
5. 5
   ろ過filtered
6. 6
   その他evaporated
7. 7
   その他Purification by flash chromatography on silica gel (25% ethyl acetate/hexanes)

実験手順

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%).

出典