Water → HCID 70046826, compound

HRID 233643Notes

Reaction equation

HRID 233643 reaction equation
[H-].[Na+].[OH:3][CH2:4][CH2:5][N:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.S(O[CH2:22][CH2:23][O: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:6]1([CH2:5][CH2:4][O:3][CH2:22][CH2:23][O: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)[CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 762881-PyrrolidineethanolHCID 86748784HCID 86748784, compound

Product 1

HCID 70046826HCID 70046826, compoundYield 86.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  1. additionwere added at room temperature in a nitrogen atmosphere
  2. temperatureat reflux for 2 hrs
  3. addition7, were added
  4. temperatureat reflux temperature for 4 hrs
  5. extractionThe residue was extracted with methylene chloride
  6. washthe organic layer was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customevaporated to dryness under reduced pressure
  9. customThe crude product was purified by flash-chromatography (SiO2)

Sources & evidence

ORD record
ord-4621b55fb6bf4bc8a2356ed01ef0a08b
Source dataset
uspto-grants-1997_01
Patent number
US05593982

Reaction notes

Loading…