Methanol → 16-Fluoroandrostan-17-one

HRID 466511Notes

Reaction equation

HRID 466511 reaction equation
[H][H].[F:3][C@H:4]1[CH2:9][C@H:8]2[C@H:10]3[C@H:20]([CH2:21][CH2:22][C@:6]2([CH3:7])[C:5]1=[O:23])[C@:18]1([CH3:19])[C@H:13]([CH2:14][CH2:15][CH2:16][CH2:17]1)[CH2:12][CH2:11]3.CO.[OH-].[K+]>C(O)C.[Pd]>[F:3][C@@H:4]1[CH2:9][C@H:8]2[C@H:10]3[C@H:20]([CH2:21][CH2:22][C@:6]2([CH3:7])[C:5]1=[O:23])[C@:18]1([CH3:19])[C@H:13]([CH2:14][CH2:15][CH2:16][CH2:17]1)[CH2:12][CH2:11]3

Participants

7

Reactant 4

HCID 887MethanolHCID 14797Potassium HydroxideHCID 54021045HCID 54021045, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18869516-Fluoroandrostan-17-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

250 mg of 16βfluoro-5-α-androsten-17-one in 50 ml of ethanol was treated with 50 mg of 5% palladium on carbon and hydrogen gas for 21/2 hours. The reaction mixture, as indicated by the IR, is compatible with 16β-fluoro-5α-androstan-17-one. This crude product was treated with 5 ml methanol and 5 ml of 1N methanolic KOH for one hour. The mixture was partitioned between methylene chloride and water and subjected to HPLC as indicated above. Crystallization of the less mobile component from methanol gave 30 mg of 16α-fluoro-5α-androstan-17-one as prismatic needles, melting point 148°-150° C.

Workup

  1. customThe mixture was partitioned between methylene chloride and water
  2. customCrystallization of the less mobile component from methanol

Sources & evidence

ORD record
ord-31922c3b39a0468d9a035d09182c21c5
Source dataset
uspto-grants-1992_10
Patent number
US05157031

Reaction notes

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