7-Oxodehydroepiandrosterone 3-acetate → 3beta-Acetoxyandrostane-7,17-dione

HRID 1912706

Reaction equation

HRID 1912706 reaction equation
[C:1]([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C:7](=[CH:8][C:9](=[O:25])[C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][C:14]2=[O:24])[CH2:6]1)(=[O:3])[CH3:2]>CCO.[Pd]>[C:1]([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[CH:7]([CH2:8][C:9](=[O:25])[C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][C:14]2=[O:24])[CH2:6]1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 97982297-Oxodehydroepiandrosterone 3-acetate

Product 1

HCID 690113133beta-Acetoxyandrostane-7,17-dioneYield 60%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3β-acetoxyandrost-5-ene-7,17-dione (7.97 g) and 10% Pd/C (0.80 g) in EtOH (0.5 L) was stirred under H2 at atm pressure for 2 h. The mixture was filtered through Celite and the filtrate evaporated to dryness. The crude product was crystallized from Et2O to give 3β-acetoxyandrostane-7,17-dione (4.75 g, 60%). 1H-NMR (300 MHz, acetone-d6, ppm from TMS): δ 4.57 (m, 1H), 2.66-0.96 (m, 20H), 1.96 (s, 3H), 1.05 (s, 3H), 0.77 (s, 3H).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customthe filtrate evaporated to dryness
  3. customThe crude product was crystallized from Et2O

Sources & evidence

ORD record
ord-56109327a9f54d8daea67e711a8c8e93
Source dataset
uspto-grants-2013_12
Patent number
US08609644B2

Linked notes

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