Water → 3beta-(2-(2-(1-Pyrrolidinyl)ethoxy)ethylthio)-17beta-(3-furyl)-5beta-androstan-14beta-ol

HRID 233648Notes

Reaction equation

HRID 233648 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:8][CH2:7][CH2:6][CH2:5]1.[H-].[Na+].S(O[CH2:22][CH2:23][S:24][C@H:25]1[CH2:42][CH2:41][C@@:40]2([CH3:43])[C@H:27]([CH2:28][CH2:29][C@@H:30]3[C@@H:39]2[CH2:38][CH2:37][C@@:35]2([CH3:36])[C@:31]3([OH:49])[CH2:32][CH2:33][C@@H:34]2[C:44]2[CH:48]=[CH:47][O:46][CH:45]=2)[CH2:26]1)(C1C=CC(C)=CC=1)(=O)=O.O>CN(C)C=O>[N:4]1([CH2:3][CH2:2][O:1][CH2:22][CH2:23][S:24][C@H:25]2[CH2:42][CH2:41][C@@:40]3([CH3:43])[C@H:27]([CH2:28][CH2:29][C@@H:30]4[C@@H:39]3[CH2:38][CH2:37][C@@:35]3([CH3:36])[C@:31]4([OH:49])[CH2:32][CH2:33][C@@H:34]3[C:44]3[CH:48]=[CH:47][O:46][CH:45]=3)[CH2:26]2)[CH2:8][CH2:7][CH2:6][CH2:5]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 762881-PyrrolidineethanolHCID 867487853beta-(2-Tosyioxyethylthio)-17beta-(3-furyl)-5beta-androstan-14beta-ol

Product 1

HCID 700458013beta-(2-(2-(1-Pyrrolidinyl)ethoxy)ethylthio)-17beta-(3-furyl)-5beta-androstan-14beta-olYield 69.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

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.

Workup

  1. temperatureat reflux for 2 hrs
  2. temperatureat reflux temperature for 4 hrs
  3. extractionThe residue was extracted with methylene chloride
  4. washthe organic layer was washed with water to neutral pH
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated to dryness under reduced pressure
  7. customThe crude product was purified by flash-chromatography (SiO2)

Sources & evidence

ORD record
ord-897f6161c38744eb8c0a119cf19709b1
Source dataset
uspto-grants-1997_01
Patent number
US05593982

Reaction notes

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