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

HRID 1733089Notes

Reaction equation

HRID 1733089 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 17β,19-dihydroxy-1α-methyl-4-androsten-3-one 3-ethylenethioketal in methanol and the resulting suspension is refluxed for four hours with rapid stirring. The suspension is cooled, filtered and the solvent evaporated. The remaining residue is chromatographed on silica gel and eluted with methylenechloride. Recrystallization from acetone-hexane yields the compound 1α-methyl-4-androstene-17β,19-diol.

Workup

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

Sources & evidence

ORD record
ord-cbfcb143d3224470bf11660ee88b0c4a
Source dataset
uspto-grants-1980_12
Patent number
US04239681

Reaction notes

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