反応 #604080

反応方程式

tert-butyl (2-bromoethyl)carbamate

dimethyl 2-(cis-4-((tert-butyldimethylsilyl)oxy)cyclohexyl)-3-(4-hydroxybenzyl)maleate

cesium carbonate

→

title compound

収率 44.0%

Dimethyl 2-(4-(2-((tert-butoxycarbonyl)amino)ethoxy)benzyl)-3-(cis-4-((tert-butyldimethylsilyl)oxy)cyclohexyl)maleate

収率 44.0%

溶媒

DMF

DMF

water

反応条件

後処理

1. 1
   抽出was extracted with ethyl acetate
2. 2
   洗浄the organic layer was washed with saturated brine
3. 3
   乾燥was dried over anhydrous sodium sulfate
4. 4
   その他the filtrate was removed by distillation under reduced pressure
5. 5
   その他The residue was chromatographed on silica gel column (hexane:ethyl acetate=8:2)

実験手順

A suspension of dimethyl 2-(cis-4-((tert-butyldimethylsilyl)oxy)cyclohexyl)-3-(4-hydroxybenzyl)maleate (35 mg, 0.075 mmol) and cesium carbonate (27 mg, 0.083 mmol) in DMF (1.2 ml) was cooled to 0° C., a solution of tert-butyl (2-bromoethyl)carbamate (20 mg, 0.091 mmol) in DMF (0.5 ml) was added dropwise, and the mixture was stirred at room temperature for 19 hr. The reaction mixture was diluted with water and was extracted with ethyl acetate, the organic layer was washed with saturated brine and was dried over anhydrous sodium sulfate, and the filtrate was removed by distillation under reduced pressure. The residue was chromatographed on silica gel column (hexane:ethyl acetate=8:2) to give the title compound as an oil (20 mg, yield 43%).

出典