Reacción #70370

ord-c75a8bd2bdce4099a50b6c51e50435ab

Ecuación de reacción

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=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)CC1/C(=N/O)C[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
title compound
Rendimiento 70.0%
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
Rendimiento 70.0%

Reactantes

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=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

Reactivos

Ninguno

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    LavadoThe combined organic extracts were washed with H2O
  2. 2
    Otrodried
  3. 3
    Otroevaporated to dryness
  4. 4
    OtroThe residue was purified by flash chromatography (SiO2, n-hexane/acetone 70/30)

Procedimiento

The title compound II-ah was prepared in 70% yield from 3,3:17,17-bis(ethylendioxy)-6-(E)-hydroxyiminoandrostane by the procedure described above for the preparation of 6-methyleneandrostane-3,17-dione (II-ac, Prepn. 13). The combined organic extracts were washed with H2O, dried and evaporated to dryness. The residue was purified by flash chromatography (SiO2, n-hexane/acetone 70/30). 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 10.61 (1H, s), 3.29 (1H, dd), 2.61-1.03 (19H, m), 0.88 (3H, s), 0.79 (3H, s).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08536160B2uspto-grants-2013_09