Reaktion #70396

ord-fc9d2af0f2a4417086853d0df6127548

Reaktionsgleichung

C[C@]12CCCCC1C[C@@H](CO)[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC13OCCOC12OCCO3
17,17-bis(ethylendioxy)-7α-hydroxymethyl-androstane
C=C1C[C@@H]2[C@H](CC[C@]3(C)C(=O)CC[C@@H]23)[C@@]2(C)CCC(=O)CC12
6-methyleneandrostane-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
7α-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)-7α-hydroxymethyl-androstane
C=C1C[C@@H]2[C@H](CC[C@]3(C)C(=O)CC[C@@H]23)[C@@]2(C)CCC(=O)CC12
6-methyleneandrostane-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

7α-Hydroxymethylandrostane-3,17-dione II-av was prepared in 85% yield from 3,3:17,17-bis(ethylendioxy)-7α-hydroxymethyl-androstane by the procedure described above for the preparation of 6-methyleneandrostane-3,17-dione (I-ac, Prepn. 13). 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 3.71 (2H, m), 3.30 (1H, t), 2.50-1.25 (21H, m), 1.12 (3H, s), 0.85 (3H, s).

Quelle

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