Dihydrotestosterone → 3beta-Amino-17beta-hydroxy-5alpha-androstane

HRID 375671

Reaktionsgleichung

Reaktionsgleichung von HRID 375671
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]2[C@H:8]3[C@H:18]([CH2:19][CH2:20][C@:3]12[CH3:4])[C@:16]1([CH3:17])[C@H:11]([CH2:12][C:13](=O)[CH2:14][CH2:15]1)[CH2:10][CH2:9]3.C([O-])(=O)C.[NH4+].C([BH3-])#[N:28].[Na+]>CO>[NH2:28][C@H:13]1[CH2:14][CH2:15][C@@:16]2([CH3:17])[C@@H:11]([CH2:10][CH2:9][C@@H:8]3[C@@H:18]2[CH2:19][CH2:20][C@@:3]2([CH3:4])[C@H:5]3[CH2:6][CH2:7][C@@H:2]2[OH:1])[CH2:12]1

Komponenten

5

Edukt 3

HCID 10635DihydrotestosteroneHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydride

Produkt 1

HCID 146048433beta-Amino-17beta-hydroxy-5alpha-androstane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

3β-Amino-17β-hydroxy-5α-androstane was prepared by the procedure of Boutigue et al. (1973, Bull. Soc. Chim. France 750-753). 17β-Hydroxy-5α-androstan-3-one (403 mg, 1.39 mmol) (Aldrich Chemical Company) was added to 862 mg of ammonium acetate (11.2 mmol, 8.06 equiv.) in 16.0 mL dry methanol (MeOH), followed by 104 mg (1.65 mmol, 1.19 equiv.) of sodium cyanoborohydride. After stirring at room temperature for 15 h, the reaction was concentrated under reduced pressure. The residue was partitioned between methylene chloride and aqueous 1N sodium hydroxide (NaOH), shaken, and separated. The organic layer was washed with water, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The product was used without further purification.

Aufarbeitung

  1. concentrationthe reaction was concentrated under reduced pressure
  2. customThe residue was partitioned between methylene chloride and aqueous 1N sodium hydroxide (NaOH)
  3. stirringshaken
  4. customseparated
  5. washThe organic layer was washed with water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe product was used without further purification

Quellen und Nachweise

ORD-Eintrag
ord-2c69af2d6d98497e8dfa90838e952f9f
Quelldatensatz
uspto-grants-1996_01
Patentnummer
US05486603

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