تفاعل #9335

معادلة التفاعل

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

المردود 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

المردود 61.9%

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGThe resulting mixture was stirred at room temperature for 45 min.
2. 2
   استخلاصThe resulting mixture was extracted with ethyl acetate (3×40 mL)
3. 3
   غسيلthe combined ethyl acetate solution was washed with brine
4. 4
   تجفيفThe solution was then dried (Na2SO4)
5. 5
   ترشيحfiltered
6. 6
   أخرىevaporated
7. 7
   أخرىPurification by flash chromatography on silica gel (25% ethyl acetate/hexanes)

الإجراء التجريبي

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%).

المصدر