Reaktion #1999902

ord-e711a1f4d1fe4672a4f745a86ba8be43

Reaktionsgleichung

C[C@]12CCCCC1C[C@H](CO)[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC13OCCOC12OCCO3
17,17-bis(ethylendioxy)-7β-hydroxymethylandrostane
C[C@]12CCC(=O)CC1[C@@H](C#N)C[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
6α-cyanoandrostane-3,17-dione
→
C[C@]12CCC(=O)CC1C[C@H](CO)[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
7β-Hydroxymethylandrostane-3,17-dione
Ausbeute 85.0%

Edukte

C[C@]12CCCCC1C[C@H](CO)[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC13OCCOC12OCCO3
17,17-bis(ethylendioxy)-7β-hydroxymethylandrostane
C[C@]12CCC(=O)CC1[C@@H](C#N)C[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
6α-cyanoandrostane-3,17-dione

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    WaschenThe combined organic extracts were washed with H2O
  2. 2
    Trocknendried over Na2SO4
  3. 3
    Sonstigeevaporated to dryness

Vorschrift

7β-Hydroxymethylandrostane-3,17-dione (II-by) was prepared in 85% yield from 3,3:17,17-bis(ethylendioxy)-7β-hydroxymethylandrostane by the procedure described above for the preparation of 6α-cyanoandrostane-3,17-dione (II-ac, Prepn. 3). The combined organic extracts were washed with H2O, dried over Na2SO4 and evaporated to dryness. 1H-NMR (300 MHz, acetone-d6, ppm from TMS): δ 3.66 (m, 2H), 3.64 (t, 1H), 2.51-0.80 (m, 21H), 1.07 (s, 3H), 0.89 (s, 3H)

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08609644B2uspto-grants-2013_12