Water → HCID 9844021, compound

HRID 233638Notes

Reaction equation

HRID 233638 reaction equation
C1(=O)[N:5]([CH2:6][CH2:7][O:8][C@H:9]2[CH2:26][CH2:25][C@@:24]3([CH3:27])[C@H:11]([CH2:12][CH2:13][C@@H:14]4[C@@H:23]3[CH2:22][CH2:21][C@@:19]3([CH3:20])[C@:15]4([OH:33])[CH2:16][CH2:17][C@@H:18]3[C:28]3[CH:32]=[CH:31][O:30][CH:29]=3)[CH2:10]2)C(=O)C2=CC=CC=C12.O.NN.O>C(O)C>[NH2:5][CH2:6][CH2:7][O:8][C@H:9]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[C@H:11]([CH2:12][CH2:13][C@@H:14]3[C@@H:23]2[CH2:22][CH2:21][C@@:19]2([CH3:20])[C@:15]3([OH:33])[CH2:16][CH2:17][C@@H:18]2[C:28]2[CH:32]=[CH:31][O:30][CH:29]=2)[CH2:10]1

Participants

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 70044124HCID 70044124, compound

Product 1

HCID 9844021HCID 9844021, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 0.50 g of 3β-(2-phthalimidoethoxy)-17β-(3-furyl)-5β-androstan-14β-ol in 50 ml of ethanol (96%) 0.19 g of hydrazine hydrate were added at room temperature. The mixture was kept at reflux for 4 hrs, then 10 ml of water were added and the ethanol distilled under reduced pressure. The residue was extracted with methylene chloride, the organic solution was washed with water, dried over anhydrous sodium sulfate and evaporated to dryness under reduced pressure. The crude residue was purified by flash-chromatography (SiO2) using methylene chloride/methanol 90/10 as eluant to give 0.35 g of the title compound (I-aa) as a white solid.

Workup

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

Sources & evidence

ORD record
ord-0e04e411c2934cb38e63c3a96fceec3c
Source dataset
uspto-grants-1997_01
Patent number
US05593982

Reaction notes

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