反应 #320830

反应方程式

water

3β-(2-tosyloxyethylthio)-17β-(3-furyl)-5β-androstan-14β-ol

1-(2-hydroxyethyl)pyrrolidine

NaH

→

title compound

收率 69.8%

3β-(2-(2-(1-Pyrrolidinyl)ethoxy)ethylthio)-17β-(3-furyl)-5β-androstan-14β-ol

收率 69.8%

溶剂

dimethylformamide

dimethylformamide

反应条件

后处理

1. 1
   温度at reflux for 2 hrs
2. 2
   温度at reflux temperature for 4 hrs
3. 3
   萃取The residue was extracted with methylene chloride
4. 4
   洗涤the organic layer was washed with water to neutral pH
5. 5
   干燥dried over anhydrous sodium sulfate
6. 6
   其他evaporated to dryness under reduced pressure
7. 7
   其他The crude product was purified by flash-chromatography (SiO2)

实验过程

To a solution of 0.21 g of 1-(2-hydroxyethyl)pyrrolidine in 5 ml of dimethylformamide, 0.076 g of NaH (60% dispersion in mineral oil) were added and the mixture was kept at reflux for 2 hrs, then 0.35 g of 3β-(2-tosyloxyethylthio)-17β-(3-furyl)-5β-androstan-14β-ol in 2 ml of dimethylformamide was added, the mixture was kept at reflux temperature for 4 hrs and 5 ml of water were added. The residue was extracted with methylene chloride, the organic layer was washed with water to neutral pH, dried over anhydrous sodium sulfate and evaporated to dryness under reduced pressure. The crude product was purified by flash-chromatography (SiO2) using methylene chloride/methanol 95/5 as eluant to give 0.22 g of the title compound (I-bz) as a white pasty solid.

来源