반응 #67888

반응 방정식

potassium hydroxide

9-borabicyclo[3,3,1]nonane

((1R,2R,3R)-3-(3-(benzyloxy)benzyl)-2-((S)-3-(tert-butyldimethylsilyloxy)octyl)-4-methylenecyclopentyloxy)(tert-butyl)dimethylsilane

hydrogen peroxide

→

titled compound

수율 78.0%

((1S,2S,3R,4R)-2-(3-(benzyloxy)benzyl)-4-(tert-butyldimethylsilyoxy)-3-((S)-3-(tert-butyl dimethylsilyoxy)octyl)cyclopentyl)methanol

수율 78.0%

용매

THF

반응 조건

후처리

1. 1
   workup.STIRRINGThe resulting suspension was stirred for one hour at room temperature
2. 2
   추출The mixture was extracted with EtOAc
3. 3
   세척the organic layer was washed with 20 ml brine
4. 4
   건조dried over MgSO4
5. 5
   기타evaporated
6. 6
   기타The resulting residue was purified by chromatography on a silica gel column

실험 절차

A degassed solution of ((1R,2R,3R)-3-(3-(benzyloxy)benzyl)-2-((S)-3-(tert-butyldimethylsilyloxy)octyl)-4-methylenecyclopentyloxy)(tert-butyl)dimethylsilane (0.75 g, 1.15 mmol) in 8 ml dry THF was cooled to 0° C. under nitrogen, and 9-borabicyclo[3,3,1]nonane (6.9 ml, 0.5M in THF) was dropwise added to the mixture. The colorless solution was stirred for overnight at 0° C. and treated with 30% hydrogen peroxide (3 ml) followed by 3N potassium hydroxide (3 ml). The resulting suspension was stirred for one hour at room temperature. The mixture was extracted with EtOAc, and the organic layer was washed with 20 ml brine, dried over MgSO4, and evaporated. The resulting residue was purified by chromatography on a silica gel column using hexane-EtOAc as eluent to give the titled compound: 0.6 g (yield 78%)

출처