3-Ethoxy-1alpha-methyl-3,5-androstadien-17beta,19-diol dipropionate → 17beta,19-Dihydroxy-1alpha-methyl-5alpha-androstan-3-one dipropionate

HRID 1834965Notes

Reaction equation

HRID 1834965 reaction equation
[C:1]([O:5][C@H:6]1[CH2:11][CH2:10][C@H:9]2[C@H:12]3[C@H:27]([CH2:28][CH2:29][C@:7]12[CH3:8])[C@:20]1([CH2:21][O:22]C(=O)CC)[C:15]([CH:16]=[C:17]([O:31]CC)[CH2:18][C@@H:19]1[CH3:30])=[CH:14][CH2:13]3)(=[O:4])[CH2:2][CH3:3]>C(OCC)(=O)C.[Pt]=O>[C:1]([OH:5])(=[O:4])[CH2:2][CH3:3].[C:1]([OH:5])(=[O:4])[CH2:2][CH3:3].[OH:5][C@H:6]1[CH2:11][CH2:10][C@H:9]2[C@H:12]3[C@H:27]([CH2:28][CH2:29][C@:7]12[CH3:8])[C@:20]1([CH2:21][OH:22])[C@H:15]([CH2:16][C:17](=[O:31])[CH2:18][C@@H:19]1[CH3:30])[CH2:14][CH2:13]3

Participants

4

Reactant 1

HCID 706145673-Ethoxy-1alpha-methyl-3,5-androstadien-17beta,19-diol dipropionate

Product 1

HCID 8673542517beta,19-Dihydroxy-1alpha-methyl-5alpha-androstan-3-one dipropionate

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-ethoxy-1α-methyl-3,5-androstadien-17β,19-diol dipropionate in ethyl acetate is hydrogenated with platinum oxide at atmospheric pressure. The solution is filtered and the solvent removed under reduced pressure. The residue is taken up in aqueous methanol containing a drop of hydrochloric acid and stirred for 20 minutes at room temperature. The methanol is removed and ether added. The ether extract is washed with water, dried over magnesium sulfate and concentrated. Crystallization of the residue from an acetone-hexane solution yields 17β,19-dihydroxy-1α-methyl-5α-androstan-3-one dipropionate.

Workup

  1. filtrationThe solution is filtered
  2. customthe solvent removed under reduced pressure
  3. customThe methanol is removed
  4. additionether added
  5. extractionThe ether extract
  6. washis washed with water
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated
  9. customCrystallization of the residue from an acetone-hexane solution

Sources & evidence

ORD record
ord-f62107a7bb724163a685a59ee4b8454d
Source dataset
uspto-grants-1978_01
Patent number
US04071625

Reaction notes

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