Reaktion #70386

ord-61c03a0824cc445b93973dcacbb44717

Reaktionsgleichung

CC(=O)O[C@H]1CC[C@@]2(C)C(CC(=O)[C@@H]3[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]32)C1
3β-acetoxyandrostane-7,17-dione
→
C[C@]12CC[C@H](O)CC1CC(=O)[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
3β-hydroxyandrostane-7,17-dione
Ausbeute 95.0%

Edukte

CC(=O)O[C@H]1CC[C@@]2(C)C(CC(=O)[C@@H]3[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]32)C1
3β-acetoxyandrostane-7,17-dione

Reagenzien

Keine

Lösungsmittel

CO
MeOH
[Na+].[OH-]
NaOH

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigewas evaporated
  2. 2
    Extraktionthe residue extracted with CH2Cl2 (2×)
  3. 3
    WaschenThe combined organic extracts were washed with brine
  4. 4
    Trocknendried over Na2SO4
  5. 5
    Filtrationfiltered
  6. 6
    Sonstigeevaporated to dryness

Vorschrift

To a solution of 3β-acetoxyandrostane-7,17-dione in MeOH (156 mL), 5N NaOH (54 mL) was added. After stirring at room temperature for 10 min the solution was evaporated and the residue extracted with CH2Cl2 (2×). The combined organic extracts were washed with brine, dried over Na2SO4, filtered and evaporated to dryness to give 3β-hydroxyandrostane-7,17-dione (1.70 g, 95%). 1H-NMR (300 MHz, acetone-d6, ppm from TMS): δ 4.56 (1H, d), 3.35 (1H, m), 2.66-0.87 (20H, m), 1.02 (3H, s), 0.76 (3H, s).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08536160B2uspto-grants-2013_09