Hydrochloric Acid → Nandrolone

HRID 1415030

Reaktionsgleichung

Reaktionsgleichung von HRID 1415030
C[O:2][C:3]1[CH2:4][C:5]2[CH2:6][CH2:7][C@@H:8]3[C@@H:17]([C:18]=2[CH2:19][CH:20]=1)[CH2:16][CH2:15][C@@:13]1([CH3:14])[C@H:9]3[CH2:10][CH2:11][C@@H:12]1[OH:21].Cl.O>CO>[OH:21][C@H:12]1[CH2:11][CH2:10][C@H:9]2[C@H:8]3[C@H:17]([CH2:16][CH2:15][C@:13]12[CH3:14])[C@@H:18]1[C:5](=[CH:4][C:3](=[O:2])[CH2:20][CH2:19]1)[CH2:6][CH2:7]3

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 1019633-Methoxyestra-2,5(10)-dien-17beta-ol

Produkt 1

HCID 9904NandroloneAusbeute 46,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Dissolve dl-3-methoxyestra-2,5(10)-dien-17β-ol (0.84 g) in methanol (18 ml) containing concentrated hydrochloric acid (1.2 ml) and water (0.8 ml) and allow the mixture to stand at room temperature for 15 hours. Add water and extract the mixture with ether. Wash, dry and evaporate the ethanol solution and dissolve the residue in a little benzene. Filter through a column of alumina (25 g) with benzene-ether (7.3). Evaporate the eluates and recrystallize the residue from etherhexane to obtain the title compound (372 mg), m.p. 123°-124.5° or in an alternate form, m.p. 131°-132°; ultraviolet absorption maximum at 241 mμ (ε16,600); infrared absorption peaks at 6μ, 7.9 μ, 9.4 μ.

Aufarbeitung

  1. extractionAdd water and extract the mixture with ether
  2. washWash
  3. customdry
  4. customevaporate the ethanol solution
  5. dissolutiondissolve the residue in a little benzene
  6. filtrationFilter through a column of alumina (25 g) with benzene-ether (7.3)
  7. customEvaporate the eluates
  8. customrecrystallize the residue from etherhexane

Quellen und Nachweise

ORD-Eintrag
ord-cd98582589444bf6a18cf5b2e53ead1e
Quelldatensatz
uspto-grants-1977_01
Patentnummer
US04002746

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