Dehydroepiandrosterone → Androst-5-ene-3,17-dione

HRID 1912666Notes

Reaction equation

HRID 1912666 reaction equation
[OH:1][C@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C:4](=[CH:5][CH2:6][C@@H:7]3[C@@H:16]2[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH2:10][C:11]2=[O:21])[CH2:3]1>C1COCC1>[CH3:13][C@:12]12[CH2:14][CH2:15][C@H:16]3[C@@H:7]([CH2:6][CH:5]=[C:4]4[C@:17]3([CH3:20])[CH2:18][CH2:19][C:2](=[O:1])[CH2:3]4)[C@@H:8]1[CH2:9][CH2:10][C:11]2=[O:21]

Participants

3

Reactant 1

HCID 5881Dehydroepiandrosterone

Product 1

HCID 160531Androst-5-ene-3,17-dioneYield 67.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3β-hydroxyandrost-5-en-17-one (13.0 g) and IBX (25.3 g) in THF (260 mL) was heated at reflux under stirring for 4 h. After cooling to room temperature, the mixture was filtered and the solid washed with EtOAc (3×50 mL). The filtrate was evaporated to dryness. The residue was taken up with CH2Cl2 and the suspension filtered. The filtrate was evaporated to dryness and the residue triturated with Et2O/MeOH 9/1 (65 mL). After filtration and drying under vacuum, 5-androstene-3,17-dione (8.68 g, 67%) was obtained. 1H-NMR (300 MHz, acetone-d6, ppm from TMS): δ 5.40 (m, 1H), 3.41 (m, 1H), 2.76-1.06 (m, 18H), 1.29 (s, 3H), 0.91 (s, 3H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. filtrationthe mixture was filtered
  4. washthe solid washed with EtOAc (3×50 mL)
  5. customThe filtrate was evaporated to dryness
  6. filtrationthe suspension filtered
  7. customThe filtrate was evaporated to dryness
  8. customthe residue triturated with Et2O/MeOH 9/1 (65 mL)
  9. filtrationAfter filtration
  10. customdrying under vacuum

Sources & evidence

ORD record
ord-6cfaaeb8f03546ee9f24d0e5483696d6
Source dataset
uspto-grants-2013_12
Patent number
US08609644B2

Reaction notes

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