Reaktion #70385

ord-8ea5bc7bec0a461b8c2c7dd3bfaac27e

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-acetoxyandrost-5-ene-7,17-dione
→
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
Ausbeute 60.0%

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-acetoxyandrost-5-ene-7,17-dione

Reagenzien

[Pd]
Pd/C

Lösungsmittel

CCO
EtOH

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    FiltrationThe mixture was filtered through Celite
  2. 2
    Sonstigethe filtrate evaporated to dryness
  3. 3
    SonstigeThe crude product was crystallized from Et2O

Vorschrift

A mixture of 3β-acetoxyandrost-5-ene-7,17-dione (7.97 g) and 10% Pd/C (0.80 g) in EtOH (0.5 L) was stirred under H2 at atm pressure for 2 h. The mixture was filtered through Celite and the filtrate evaporated to dryness. The crude product was crystallized from Et2O to give 3β-acetoxyandrostane-7,17-dione (4.75 g, 60%) 1H-NMR (300 MHz, acetone-d6, ppm from TMS): δ 4.57 (1H, m), 2.66-0.96 (20H, m), 1.96 (3H, s), 1.05 (3H, s), 0.77 (3H, s).

Quelle

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