Reacción #70391

ord-0ac52c358f8e452fa7029acca43964ea

Ecuación de reacción

CO/N=C1\CC2CCCC[C@]2(C)[C@H]2CC[C@@]3(C)[C@@H](CC45OCCOC43OCCO5)[C@H]12
17,17-bis(ethylendioxy)-7-(E)-methoxyiminoandrostane
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
→
CO/N=C1\CC2CC(=O)CC[C@]2(C)[C@H]2CC[C@]3(C)C(=O)CC[C@H]3[C@H]12
title compound
Rendimiento 55.0%
CO/N=C1\CC2CC(=O)CC[C@]2(C)[C@H]2CC[C@]3(C)C(=O)CC[C@H]3[C@H]12
7-(E)-Methoxyiminoandrostane-3,17-dione
Rendimiento 55.0%

Reactantes

CO/N=C1\CC2CCCC[C@]2(C)[C@H]2CC[C@@]3(C)[C@@H](CC45OCCOC43OCCO5)[C@H]12
17,17-bis(ethylendioxy)-7-(E)-methoxyiminoandrostane
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
    OtroThe crude product was purified by flash chromatography (SiO2, n-hexane/EtOAc 6/4)

Procedimiento

The title compound II-au was prepared in 55% yield from 3,3:17,17-bis(ethylendioxy)-7-(E)-methoxyiminoandrostane by the procedure described above for the preparation of 6-methyleneandrostane-3,17-dione (II-ac, Prepn. 13). The crude product was purified by flash chromatography (SiO2, n-hexane/EtOAc 6/4). 1H-NMR (300 MHz, DMSO-d6, ppm from TMS: δ 3.72 (3H, s), 2.89 (1H, m), 2.63-0.93 (19H, m), 1.12 (3H, s), 0.82 (3H, s).

Fuente

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