HCID 21722881, compound → 14alpha-Fluoro-3beta-hydroxy-5alpha-androstan-17-one

HRID 894503Notes

Reaction equation

HRID 894503 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@@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

Participants

5

Reactant 2

HCID 21722881HCID 21722881, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 7057105414alpha-Fluoro-3beta-hydroxy-5alpha-androstan-17-oneYield 39.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

14α-Fluoro-3β-hydroxyandrost-5(6)-en-17-one (400 mg) 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 14α-fluoro-3β-hydroxy-5α-androstan-17-one (158 mg) m.p. 201°-202°; [α]D23 +83° (c 0.84, CHCl3); vmax 3500 and 1730 cm-1 ; the PMR spectrum included signals at δ0.83 (3H, s, 19-Me), 1.00 (3H, s, 18-Me) and 3.6 (1H, m, 3-CHOH); FMR φ*+164 ppm (broad multiplet ca 80 Hz wide).

Workup

  1. custom(72 hr)
  2. customThe solvent was evaporated in vacuo
  3. customthe crude product was recrystallised from acetone

Sources & evidence

ORD record
ord-e3b559a29be447bc8b464292f263d051
Source dataset
uspto-grants-1981_08
Patent number
US04284558

Reaction notes

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