반응 #320826

반응 방정식

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

1-(2-mercaptoethyl)pyrrolidine

sodium hydride

→

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

용매

DMF

dimethylformamide

반응 조건

후처리

1. 1
   workup.ADDITION7, was added
2. 2
   workup.STIRRINGthe mixture was stirred for another 4 hrs
3. 3
   기타the reaction mixture was quenched with water
4. 4
   추출extracted with methylene chloride
5. 5
   세척The organic layer was washed with water
6. 6
   건조dried over anhydrous sodium sulfate
7. 7
   기타evaporated to dryness under reduced pressure
8. 8
   기타The crude product was purified by flash-cromatography (SiO2)

실험 절차

To a solution of 0.28 g of 1-(2-mercaptoethyl)pyrrolidine in 20 ml of dimethylformamide, 0.086 g of sodium hydride (60% dispersion in mineral oil) were added under nitrogen atmosphere, and the mixture stirred at room temperature for half an hr; a DMF solution of 1.0 g of 3β-(2-tosyloxyethoxy)-17β-(3-furyl)-5β-androstan-14β-ol, prepared as described in Ex. 7, was added and the mixture was stirred for another 4 hrs; the reaction mixture was quenched with water and 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-cromatography (SiO2) using methylene chloride/methanol 95/5 as eluant and 0.90 g of the title compound (I-ai) as a white amorphous solid.

출처