Reaktion #1999844

ord-1e8c9cf5d90a46f3a69f99a535905f02

Reaktionsgleichung

C[C@]12CCCCC1[C@@H](O[N+](=O)[O-])C[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC13OCCOC12OCCO3
17,17-bis(ethylendioxy)androstane-6α-yl nitrate
C[C@]12CCC(=O)CC1[C@@H](O[N+](=O)[O-])C[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
3,17-dioxoandrostane-6α-yl nitrate
→
C[C@]12CCC(=O)CC1[C@H](O[N+](=O)[O-])C[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
3,17-Dioxoandrostane-6-βyl nitrate

Edukte

C[C@]12CCCCC1[C@@H](O[N+](=O)[O-])C[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC13OCCOC12OCCO3
17,17-bis(ethylendioxy)androstane-6α-yl nitrate
C[C@]12CCC(=O)CC1[C@@H](O[N+](=O)[O-])C[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
3,17-dioxoandrostane-6α-yl nitrate

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigePrepared in 75% yield from 3,3
  2. 2
    SonstigeThe crude product was purified by flash chromatography (SiO2, cyclo-hexane/acetone/CH2Cl2 70/15/15)
  3. 3
    Sonstigeto give II-ab

Vorschrift

Prepared in 75% yield from 3,3:17,17-bis(ethylendioxy)androstane-6α-yl nitrate following the procedure described above for the preparation of 3,17-dioxoandrostane-6α-yl nitrate (II-aa, Prepn 1). The crude product was purified by flash chromatography (SiO2, cyclo-hexane/acetone/CH2Cl2 70/15/15) to give II-ab. 1H-NMR (300 MHz, acetone-d6, ppm from TMS): δ 5.24 (ddd, 1H), 2.72 (dd, 1H), 2.57-0.96 (m, 19H), 1.25 (s, 3H), 0.90 (s, 3H).

Quelle

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