反応 #67888

反応方程式

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

収率 78.0%

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

収率 78.0%

溶媒

THF

反応条件

後処理

1. 1
   workup.STIRRINGThe resulting suspension was stirred for one hour at room temperature
2. 2
   抽出The mixture was extracted with EtOAc
3. 3
   洗浄the organic layer was washed with 20 ml brine
4. 4
   乾燥dried over MgSO4
5. 5
   その他evaporated
6. 6
   その他The resulting residue was purified by chromatography on a silica gel column

実験手順

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%)

出典