Methanol → HCID 67615172, compound

HRID 1599977Notes

Reaction equation

HRID 1599977 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 67615172HCID 67615172, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

250 mg of 16β fluoro-5-α-androsten-17-one in 50 ml of ethanol was treated with 50 mg of 5% palladium on carbon and hydrogen gas for 21/2hours. 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 mixturewas 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 16β-fluoro-5β-androstan-17-one as prismatic needles, melting point 148°-150° C.

Workup

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

Sources & evidence

ORD record
ord-bead95b26f274d018de179a5806c6196
Source dataset
uspto-grants-1998_04
Patent number
US05744462

Reaction notes

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