Dihydrotestosterone → HCID 68730165, Verbindung

HRID 1182885

Reaktionsgleichung

Reaktionsgleichung von HRID 1182885
[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]

Komponenten

4

Edukt 2

HCID 10635DihydrotestosteroneHCID 2724933Selectfluor2×

Produkt 1

HCID 68730165HCID 68730165, VerbindungAusbeute 4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-71a0f7b11f1d47418a16ad1e29568ed0
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08664210B2

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