Reaktion #1999860

ord-d31c6ba2bda7489c8ad6297d744c352a

Reaktionsgleichung

C[C@]12CCCCC1[C@@H](CCO)C[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC13OCCOC12OCCO3
17,17-bis(ethylendioxy)-6α-(2-hydroxyethyl)androstane
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)CC1[C@@H](CCO)C[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
title compound
Ausbeute 100.0%
C[C@]12CCC(=O)CC1[C@@H](CCO)C[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
6α-(2-Hydroxyethyl)androstane-3,17-dione
Ausbeute 100.0%

Edukte

C[C@]12CCCCC1[C@@H](CCO)C[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC13OCCOC12OCCO3
17,17-bis(ethylendioxy)-6α-(2-hydroxyethyl)androstane
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

The title compound II-al was prepared in 100% yield from 3,3:17,17-bis(ethylendioxy)-6α-(2-hydroxyethyl)androstane 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, dmso-d6, ppm from TMS): δ 4.32 (t, 1H), 3.39 (m, 2H), 2.46-0.54 (m, 23H), 0.98 (s, 3H), 0.79 (s, 3H).

Quelle

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