Reaktion #70389

ord-c919640376e74a4c9f1be4016bb5e594

Reaktionsgleichung

C[C@]12CCCCC1CC(=O)[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC13OCCOC12OCCO3
17,17-bis(ethylendioxy)androstan-7-one
C[C@]12CCCCC1/C(=N/O)C[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC13OCCOC12OCCO3
17,17-bis(ethylendioxy)-6-(E)-hydroxyiminoandrostane
→
C[C@]12CCCCC1C/C(=N\O)[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC13OCCOC12OCCO3
17,17-Bis(ethylendioxy)-7-(E)-hydroxyiminoandrostane
Ausbeute 95.0%

Edukte

C[C@]12CCCCC1CC(=O)[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC13OCCOC12OCCO3
17,17-bis(ethylendioxy)androstan-7-one
C[C@]12CCCCC1/C(=N/O)C[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC13OCCOC12OCCO3
17,17-bis(ethylendioxy)-6-(E)-hydroxyiminoandrostane

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe crude product was purified by flash chromatography (SiO2, CH2Cl2/MeOH 9/1)

Vorschrift

17,17-Bis(ethylendioxy)-7-(E)-hydroxyiminoandrostane was prepared in 95% yield from 3,3:17,17-bis(ethylendioxy)androstan-7-one by the procedure described above for the preparation of 3,3:17,17-bis(ethylendioxy)-6-(E)-hydroxyiminoandrostane (Prepn. 18). The crude product was purified by flash chromatography (SiO2, CH2Cl2/MeOH 9/1). 1H-NMR (300 MHz, DMSO-d6, ppm from TMS: δ 10.17 (1H, s), 3.88-3.70 (8H, m), 2.89 (1H, m), 2.23-0.71 (19H, m), 0.90 (3H, s), 0.77 (3H, s).

Quelle

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