Pyridine → Nandrolone acetate

HRID 1608739

Reaktionsgleichung

Reaktionsgleichung von HRID 1608739
[CH3:1][C@@:2]12[C@@H:10]([OH:11])[CH2:9][CH2:8][C@H:7]1[C@@H:6]1[CH2:12][CH2:13][C:14]3[C@@H:20]([C@H:5]1[CH2:4][CH2:3]2)[CH2:19][CH2:18][C:16](=[O:17])[CH:15]=3.N1C=CC=CC=1.[C:27](Cl)(=[O:29])[CH3:28]>C(OC(=O)C)(=O)C>[CH3:28][C:27]([O:11][C@@H:10]1[C@@:2]2([CH3:1])[CH2:3][CH2:4][C@@H:5]3[C@@H:20]4[C:14](=[CH:15][C:16]([CH2:18][CH2:19]4)=[O:17])[CH2:13][CH2:12][C@H:6]3[C@@H:7]2[CH2:8][CH2:9]1)=[O:29]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 9904Nandrolone

Produkt 1

HCID 102122Nandrolone acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7918Acetic AnhydrideLösungsmittel

Versuchsvorschrift

In an apparatus supplied with a drierite drying tube, a solution of 19-nor-testosterone (10 (100 g; 0.365 mole) in acetic anhydride (200 ml), pyridine (32 ml) and acetylchloride (320 ml) was heated at reflux under magnetic stirring, for 3 h and then concentrated to dryness under vacuum. The dry residue was triturated in absolute ethanol, filtered and washed with little portions of absolute ethanol. After drying, 19-nor-testosterone acetate 3-enolacetate was obtained as a white powder (121.4 g, yield 93%) mp. 176-177° C. The structure was confirmed by spectroscopic means.

Aufarbeitung

  1. customIn an apparatus supplied with a drierite drying tube
  2. temperatureat reflux under magnetic stirring, for 3 h
  3. concentrationconcentrated to dryness under vacuum
  4. customThe dry residue was triturated in absolute ethanol
  5. filtrationfiltered
  6. washwashed with little portions of absolute ethanol
  7. customAfter drying

Quellen und Nachweise

ORD-Eintrag
ord-572418e46bd441f7b884d40c573f94a2
Quelldatensatz
uspto-grants-1995_03
Patentnummer
US05395842

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