반응 #320825

반응 방정식

water

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

NaH

1-(2-hydroxyethyl)pyrrolidine

→

title compound

수율 86.7%

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

수율 86.7%

용매

dimethylformamide

반응 조건

후처리

1. 1
   workup.ADDITIONwere added at room temperature in a nitrogen atmosphere
2. 2
   온도at reflux for 2 hrs
3. 3
   workup.ADDITION7, were added
4. 4
   온도at reflux temperature for 4 hrs
5. 5
   추출The residue was extracted with methylene chloride
6. 6
   세척the organic layer was washed with water
7. 7
   건조dried over anhydrous sodium sulfate
8. 8
   기타evaporated to dryness under reduced pressure
9. 9
   기타The crude product was purified by flash-chromatography (SiO2)

실험 절차

To a suspension of 0.13 g of NaH (60% dispersion in mineral oil) in 15 ml of anhydrous dimethylformamide, 0.37 g of 1-(2-hydroxyethyl)pyrrolidine were added at room temperature in a nitrogen atmosphere. The mixture was kept at reflux for 2 hrs, then 0.90 g of 3β-(2-tosyloxy-ethoxy)-17β-(3-furyl)-5β-androstan-14β-ol, prepared as an intermediate in Ex. 7, were added. The mixture was kept at reflux temperature for 4 hrs; then 50 ml of water were added cautiously. The residue was extracted with methylene chloride, the organic layer was washed with water, dried over anhydrous sodium sulfate and evaporated to dryness under reduced pressure. The crude product was purified by flash-chromatography (SiO2) using acetone/methanol 85/15 as eluant to give 0.70 g of the title compound (I-ah) as a light yellow solid.

출처