Acetic Acid → 3beta,14beta-Dihydroxyandrostan-17-one

HRID 1395017Notes

Reaction equation

HRID 1395017 reaction equation
[C:1]([OH:4])(=O)[CH3:2].CC(C)=[O:7].[CH3:9][C@:10]12[CH2:27][CH2:26][C@H:25]3[C@@H:15]([CH2:16][CH2:17][CH:18]4[C@:23]3([CH3:24])[CH2:22]CC[CH2:19]4)[C@@H:14]1[CH2:13][CH2:12][C:11]2=[O:28]>C(Cl)(Cl)Cl.[Pt]=O>[OH:4][C@H:1]1[CH2:2][CH2:24][C@@:23]2([CH3:22])[CH:18]([CH2:17][CH2:16][C@@H:15]3[C@@H:25]2[CH2:26][CH2:27][C@@:10]2([CH3:9])[C@:14]3([OH:7])[CH2:13][CH2:12][C:11]2=[O:28])[CH2:19]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 180AcetoneHCID 10880319Androstan-17-one

Product 1

HCID 539465913beta,14beta-Dihydroxyandrostan-17-one

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 6212ChloroformSolvent

Procedure

The hydrogenation of 14β-hydroxy-9(11)-androsten-3,17-dione (100 mg.) was carried out over 50 mg. of platinum oxide in 25 ml. of glacial acetic acid. When consumption of hydrogen had ceased, the catalyst was filtered, the solvent was evaporated under vacuum and the product was isolated by chromatography on silica gel using a mixture of 10% acetone in chloroform to afford 70 mg. (~70%) of the androstan-17-one, m.p. 214°-217°.

Workup

  1. customWhen consumption of hydrogen
  2. filtrationthe catalyst was filtered
  3. customthe solvent was evaporated under vacuum
  4. customthe product was isolated by chromatography on silica gel using
  5. customto afford 70 mg

Sources & evidence

ORD record
ord-fbf58e05b1df4d4da751c65fc33a6cbc
Source dataset
uspto-grants-1980_05
Patent number
US04201717

Reaction notes

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