Reacción #9335

Ecuación de reacción

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

Rendimiento 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

Rendimiento 61.9%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGThe resulting mixture was stirred at room temperature for 45 min.
2. 2
   ExtracciónThe resulting mixture was extracted with ethyl acetate (3×40 mL)
3. 3
   Lavadothe combined ethyl acetate solution was washed with brine
4. 4
   SecadoThe solution was then dried (Na2SO4)
5. 5
   Filtraciónfiltered
6. 6
   Otroevaporated
7. 7
   OtroPurification by flash chromatography on silica gel (25% ethyl acetate/hexanes)

Procedimiento

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%).

Fuente