Reaktion #70382

ord-b450267566264f96bf1fd740441dea73

Reaktionsgleichung

C[C@]12CC[C@H]3[C@@H](CC(=O)[C@@]4(O)CCCC[C@]34C)[C@@H]1CC13OCCOC12OCCO3
17,17-bis(ethylendioxy)-5α-hydroxyandrostan-6-one
C[C@]12CCC(=O)CC1/C(=N/O)C[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
6-(E)-hydroxyiminoandrostane-3,17-dione
→
C[C@]12CC[C@H]3[C@@H](C/C(=N\O)[C@@]4(O)CCCC[C@]34C)[C@@H]1CC13OCCOC12OCCO3
17,17-Bis(ethylendioxy)-5α-hydroxy-6-(E)-hydroxyimino-androstane
Ausbeute 85.0%

Edukte

C[C@]12CC[C@H]3[C@@H](CC(=O)[C@@]4(O)CCCC[C@]34C)[C@@H]1CC13OCCOC12OCCO3
17,17-bis(ethylendioxy)-5α-hydroxyandrostan-6-one
C[C@]12CCC(=O)CC1/C(=N/O)C[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
6-(E)-hydroxyiminoandrostane-3,17-dione

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe crude was purified by flash chromatography (SiO2, cyclohexane/acetone/CH2Cl2 70/15/15)

Vorschrift

17,17-Bis(ethylendioxy)-5α-hydroxy-6-(E)-hydroxyimino-androstane was prepared in 85% yield from 3,3:17,17-bis(ethylendioxy)-5α-hydroxyandrostan-6-one (Prepn. 26) by the procedure described above for the preparation of 6-(E)-hydroxyiminoandrostane-3,17-dione (II-ah, Prepn. 18). The crude was purified by flash chromatography (SiO2, cyclohexane/acetone/CH2Cl2 70/15/15). 1H-NMR (300 MHz, DMSO-d6, ppm from TMS: δ 10.45 (1H, s), 4.33 (1H, s), 3.96-3.69 (8H, m), 2.96 (1H, dd), 2.02-1.08 (18H, m), 0.74 (3H, s), 0.71 (3H, s).

Quelle

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