Dihydrotestosterone → 4alpha-Fluoro-17beta-hydroxyandrostan-3-one

HRID 1182885

Reaction equation

HRID 1182885 reaction equation
[CH3:1][C@@:2]12[C@H:12]3[CH2:13][CH2:14][C@:15]4([CH3:21])[C@@H:19]([OH:20])[CH2:18][CH2:17][C@H:16]4[C@@H:11]3[CH2:10][CH2:9][C@H:8]1[CH2:7][C:5](=[O:6])[CH2:4][CH2:3]2.[F:22][B-](F)(F)F.F[B-](F)(F)F.ClC[N+]12CC[N+](F)(CC1)CC2>CC(O)C>[F:22][C@@H:7]1[C:5](=[O:6])[CH2:4][CH2:3][C@@:2]2([CH3:1])[CH:8]1[CH2:9][CH2:10][C@@H:11]1[C@@H:12]2[CH2:13][CH2:14][C@@:15]2([CH3:21])[C@H:16]1[CH2:17][CH2:18][C@@H:19]2[OH:20]

Participants

4

Reactant 2

HCID 10635DihydrotestosteroneHCID 2724933Selectfluor2×

Product 1

HCID 687301654alpha-Fluoro-17beta-hydroxyandrostan-3-oneYield 4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of dihydrotestosterone (1.00 g), 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) or SELECTFLUOR® (1.92 g) in i-PrOH (35 ml) was refluxed for 18 h. After cooling, the resulting precipitate was filtered and the organic phase was washed with H2O and brine, dried over Na2SO4 and was evaporated to dryness. The crude reaction mixture was purified by flash chromatography (SiO2, n-hexane/acetone/EOAc 75/12.5/12.5) to give 4α-fluoro-17β-hydroxyandrostan-3-one (43 mg, 4% yield).

Workup

  1. temperaturewas refluxed for 18 h
  2. temperatureAfter cooling
  3. filtrationthe resulting precipitate was filtered
  4. washthe organic phase was washed with H2O and brine
  5. dry with materialdried over Na2SO4
  6. customwas evaporated to dryness
  7. customThe crude reaction mixture
  8. customwas purified by flash chromatography (SiO2, n-hexane/acetone/EOAc 75/12.5/12.5)

Sources & evidence

ORD record
ord-71a0f7b11f1d47418a16ad1e29568ed0
Source dataset
uspto-grants-2014_03
Patent number
US08664210B2

Linked notes

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