Ethanol → HCID 86736929, compound

HRID 2049487Notes

Reaction equation

HRID 2049487 reaction equation
[CH2:1]([O:3][C@H:4]1[CH2:22][C@@:21]2([CH3:23])[C@@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:20]2[C:19](=O)[CH2:18][C@@:17]2([CH3:25])[C@H:11]3[CH2:12][CH2:13]/[C:14]/2=[CH:15]/[CH3:16])[CH2:6][C@@H:5]1[OH:26])[CH3:2].C(O)C.[Cl-].[OH:31][NH3+:32]>[OH-].[Na+]>[CH2:1]([O:3][C@H:4]1[CH2:22][C@@:21]2([CH3:23])[C@@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:20]2[C:19](=[N:32][OH:31])[CH2:18][C@@:17]2([CH3:25])[C@H:11]3[CH2:12][CH2:13]/[C:14]/2=[CH:15]/[CH3:16])[CH2:6][C@@H:5]1[OH:26])[CH3:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 21645Hydroxylamine HClHCID 12796507HCID 12796507, compound

Product 1

HCID 86736929HCID 86736929, compoundYield 29.7%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of (Z)-2β-ethoxy-3α-hydroxy-5α-pregn-17(20)-en-11-one (710 mg) in refluxing ethanol (21 ml) was treated with a slurry of hydroxylammonium chloride (1.43 g) in 50% aqueous sodium hydroxide. After 24 hour refluxing, the cooled reaction mixture was partitioned between ethyl acetate and water. The organic phase was washed with water and evaporated to a froth (710 mg). This material was retreated with hydroxylamine as above to give a froth (800 mg) which was purified by preparative TLC (4% methanol in chloroform 22) and crystallisation from ethyl acetate/petrol to yield the title compound (220 mg), m.p. 176°-193°, [α]D +35.9°.

Workup

  1. temperatureAfter 24 hour refluxing
  2. customthe cooled reaction mixture
  3. customwas partitioned between ethyl acetate and water
  4. washThe organic phase was washed with water
  5. customevaporated to a froth (710 mg)
  6. customto give a froth (800 mg) which
  7. customwas purified by preparative TLC (4% methanol in chloroform 22) and crystallisation from ethyl acetate/petrol

Sources & evidence

ORD record
ord-51e676299cdf4f42ad1b9be28cdb9013
Source dataset
uspto-grants-1980_04
Patent number
US04197296

Reaction notes

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