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

HRID 2163485Notes

Reaction equation

HRID 2163485 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-ef929f317e3843c6ab0b106defe3458f
Source dataset
uspto-grants-1979_01
Patent number
US04134920

Reaction notes

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