HCID 21722881, compound → 14alpha-Fluoro-5alpha-androstane-3,17-dione

HRID 259220Notes

Reaction equation

HRID 259220 reaction equation
[F:1][C@:2]12[C@H:19]3[C@@H:10]([C@:11]4([CH3:21])[C:16](=[CH:17][CH2:18]3)[CH2:15][C@@H:14]([OH:20])[CH2:13][CH2:12]4)[CH2:9][CH2:8][C@:6]1([CH3:7])[C:5](=[O:22])[CH2:4][CH2:3]2.[H][H]>C(O)C.[Pd]>[F:1][C@:2]12[C@H:19]3[C@@H:10]([C@:11]4([CH3:21])[C@@H:16]([CH2:17][CH2:18]3)[CH2:15][C:14](=[O:20])[CH2:13][CH2:12]4)[CH2:9][CH2:8][C@:6]1([CH3:7])[C:5](=[O:22])[CH2:4][CH2:3]2

Participants

5

Reactant 2

HCID 21722881HCID 21722881, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 7057094114alpha-Fluoro-5alpha-androstane-3,17-dione

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

14α-Fluoro-3β-hydroxyandrost-5(6)-en-17-one (400mg) in ethanol (70 ml) was hydrogenated over palladium-charcoal (5%; 250 mg) until uptake of hydrogen ceased (72 hr). The solvent was evaporated in vacuo and the crude product was recrystallised from acetone: hexane to give prisms of

Workup

  1. custom(72 hr)
  2. customThe solvent was evaporated in vacuo
  3. customthe crude product was recrystallised from acetone
  4. customhexane to give prisms of

Sources & evidence

ORD record
ord-da01124c590f4b53bfcdd34f80dad778
Source dataset
uspto-grants-1977_07
Patent number
US04036864

Reaction notes

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