Reaktion #70403

ord-336c278ce5a6477a9c9ab8ff10b51851

Reaktionsgleichung

CC(C)(C)[Si](C)(C)O[C@H]1CC[C@@]2(C)C(C1)[C@@H](O)C[C@H]1[C@@H]3CC[C@H](O)[C@@]3(C)CC[C@@H]12
3β-tert-butyldimethylsilyloxyandrostane-6α,17β-diol
→
CC(C)(C)[Si](C)(C)O[C@H]1CC[C@@]2(C)C(C1)C(=O)C[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
3β-tert-butyldimethylsilyloxyandrostane-6,17-dione
Ausbeute 75.0%

Edukte

CC(C)(C)[Si](C)(C)O[C@H]1CC[C@@]2(C)C(C1)[C@@H](O)C[C@H]1[C@@H]3CC[C@H](O)[C@@]3(C)CC[C@@H]12
3β-tert-butyldimethylsilyloxyandrostane-6α,17β-diol

Reagenzien

Keine

Lösungsmittel

CS(C)=O
DMSO

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.ADDITIONwas added at room temperature
  2. 2
    SonstigeAfter 1.5 h the mixture was quenched at room temperature by addition of H2O (300 mL)
  3. 3
    FiltrationAfter 15 min the mixture was filtered
  4. 4
    Waschenthe cake was washed with H2O
  5. 5
    ExtraktionThe cake was extracted with Et2O (4×)
  6. 6
    TrocknenThe combined organic extracts were dried over Na2SO4
  7. 7
    Sonstigeevaporated to dryness

Vorschrift

To a stirred suspension of 3β-tert-butyldimethylsilyloxyandrostane-6α,17β-diol (EP 0825197 A2, 6.21 g) in DMSO (160 mL), IBX (16.45 g) was added at room temperature. After 1.5 h the mixture was quenched at room temperature by addition of H2O (300 mL). After 15 min the mixture was filtered and the cake was washed with H2O. The cake was extracted with Et2O (4×). The combined organic extracts were dried over Na2SO4 and evaporated to dryness to give 3β-tert-butyldimethylsilyloxyandrostane-6,17-dione (0.36 g, 75%). 1H-NMR (300 MHz, DMSO-d6, ppm from TMS: δ 3.54 (1H, m), 2.47-1.08 (20H, m), 0.84 (9H, s), 0.77 (3H, s), 0.66 (1H, s), 0.01 (6H, s).

Quelle

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