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

HRID 371829Notes

Reaction equation

HRID 371829 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 4 hours with rapid stirring. The suspension is cooled, filtered and the solvent evaporated. The remaining residue is chromatographed on silica gel an 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 4 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. washan eluted with methylenechloride
  7. customRecrystallization from acetone-hexane

Sources & evidence

ORD record
ord-6fa81d89cb204e4faf0ed5d65bbfc46c
Source dataset
uspto-grants-1978_05
Patent number
US04087524

Reaction notes

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