Acetic Anhydride → Nandrolone acetate

HRID 357326

Reaktionsgleichung

Reaktionsgleichung von HRID 357326
[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.[C:21](OC(=O)C)(=[O:23])[CH3:22]>N1C=CC=CC=1.C(Cl)(=O)C>[CH3:22][C:21]([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:23]

Komponenten

5

Edukt 2

HCID 7918Acetic AnhydrideHCID 9904Nandrolone

Produkt 1

HCID 102122Nandrolone acetate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6367Acetyl chlorideLösungsmittel

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-6ddf3ebc552143a58fc6967cce1d1e1a
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05840735

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