Sodium Hydroxide → HCID 88776434, compound

HRID 2049478Notes

Reaction equation

HRID 2049478 reaction equation
[CH2:1]([O:3][C@H:4]1[CH2:21][C@@:20]2([CH3:22])[C@@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:19]2[C:18](=O)[CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][C:14]32[O:27][CH2:26][CH2:25][O:24]3)[CH2:6][C@@H:5]1[OH:28])[CH3:2].Cl.[NH2:30][OH:31].[OH-].[Na+]>C(O)C>[CH2:1]([O:3][C@H:4]1[CH2:21][C@@:20]2([CH3:22])[C@@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:19]2[C:18](=[N:30][OH:31])[CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][C:14]32[O:27][CH2:26][CH2:25][O:24]3)[CH2:6][C@@H:5]1[OH:28])[CH3:2]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 12796495HCID 12796495, compound

Product 1

HCID 88776434HCID 88776434, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2β-Ethoxy-17,17-ethylenedioxy-3α-hydroxy-5α-androstan-11-one (8.2 g) was added to hydroxylamine hydrochloride (15 g) in ethanol (500 ml) containing 44% sodium hydroxide solution (90 ml). After refluxing for 24 hours about half the solvent was evaporated in vacuo and the residue was diluted with water and extracted with ethyl acetate. The washed and dried (Na2SO4) organic solution was evaporated in vacuo to afford a froth which on crystallization from ethyl acetate-petroleum ether afforded the title compound m.p. 136°-140°, [α]D +41.1°.

Workup

  1. temperatureAfter refluxing for 24 hours about half the solvent
  2. customwas evaporated in vacuo
  3. additionthe residue was diluted with water
  4. extractionextracted with ethyl acetate
  5. washThe washed
  6. dry with materialdried (Na2SO4) organic solution
  7. customwas evaporated in vacuo
  8. customto afford a froth which
  9. customon crystallization from ethyl acetate-petroleum ether

Sources & evidence

ORD record
ord-de5db9c71a50430db793fdad144936f9
Source dataset
uspto-grants-1980_04
Patent number
US04197296

Reaction notes

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