17beta,19-Dihydroxy-1alpha-methyl-4-androsten-3-one 3-ethylenethioketal → 1alpha-Methyl-4-androstene-17beta,19-diol

HRID 2397970Notes

Reaction equation

HRID 2397970 reaction equation
C1O[C:4]2([CH2:21][C@H:20]([CH3:22])[C@@:19]3([CH2:23][OH:24])[C:6]([CH2:7][CH2:8][C@@H:9]4[C@@H:18]3[CH2:17][CH2:16][C@@:14]3([CH3:15])[C@H:10]4[CH2:11][CH2:12][C@@H:13]3[OH:25])=[CH:5]2)SC1>[Ni].CO>[CH3:22][C@@H:20]1[C@@:19]2([CH2:23][OH:24])[C:6]([CH2:7][CH2:8][C@@H:9]3[C@@H:18]2[CH2:17][CH2:16][C@@:14]2([CH3:15])[C@H:10]3[CH2:11][CH2:12][C@@H:13]2[OH:25])=[CH:5][CH2:4][CH2:21]1

Participants

4

Reactant 1

HCID 2279742417beta,19-Dihydroxy-1alpha-methyl-4-androsten-3-one 3-ethylenethioketal

Product 1

HCID 705847581alpha-Methyl-4-androstene-17beta,19-diol

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

Raney nickel is added to a solution of the above 17β,19-dihydroxy-1α-methyl-4-androsten-3-one 3-ethylenethioketal in methanol and the resulting suspension is refluxed for about 4 hours with rapid stirring. The suspension is cooled, filtered and the solvent evaporated. The residue is chromatographed on silica gel and eluted with methylenechloride. Recrystallization from acetone-hexane yields 1α-methyl-4-androstene-17β,19-diol.

Workup

  1. temperaturethe resulting suspension is refluxed for about 4 hours with rapid stirring
  2. temperatureThe suspension is cooled
  3. filtrationfiltered
  4. customthe solvent evaporated
  5. customThe residue is chromatographed on silica gel
  6. washeluted with methylenechloride
  7. customRecrystallization from acetone-hexane

Sources & evidence

ORD record
ord-4d05452c6ca247f0b85211daee744714
Source dataset
uspto-grants-1977_05
Patent number
US04022769

Reaction notes

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