5alpha-Androst-7-ene-3-one-17beta-ol → 5alpha-Androst-8(14)-ene-3-one-17beta-ol

HRID 1708904Notes

Reaction equation

HRID 1708904 reaction equation
[CH3:1][C@:2]12[CH2:19][CH2:18][C@H:17]3[C:7](=[CH:8][CH2:9][C@@H:10]4[C@:15]3([CH3:16])[CH2:14][CH2:13][C:12](=[O:20])[CH2:11]4)[C@@H:6]1[CH2:5][CH2:4][C@@H:3]2[OH:21]>C(OCC)(=O)C.[Pd]>[CH3:1][C@:2]12[CH2:19][CH2:18][C@H:17]3[C:7]([CH2:8][CH2:9][C@@H:10]4[C@:15]3([CH3:16])[CH2:14][CH2:13][C:12](=[O:20])[CH2:11]4)=[C:6]1[CH2:5][CH2:4][C@@H:3]2[OH:21]

Participants

4

Reactant 1

HCID 186380785alpha-Androst-7-ene-3-one-17beta-ol

Product 1

HCID 186380795alpha-Androst-8(14)-ene-3-one-17beta-ol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5α-androst-7-ene-3-one-17β-ol in ethyl acetate is hydrogenated at room temperature and 1 atmosphere over 10% palladium on carbon for 8 hours. Filtration to remove the catalyst and concentration affords 5α-androst-8(14)-ene-3-one-17β-ol.

Workup

  1. customis hydrogenated at room temperature
  2. filtrationFiltration
  3. customto remove
  4. concentrationthe catalyst and concentration

Sources & evidence

ORD record
ord-3c63eb8d022f475092314b70b3ab5711
Source dataset
uspto-grants-1990_08
Patent number
US04946834

Reaction notes

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