Reacción #70392

ord-b09563a52f92484382a41836d55413b4

Ecuación de reacción

$C=CCO/N=C1\CC2CCCC[C@]2(C)[C@H]2CC[C@@]3(C)[C@@H](CC45OCCOC43OCCO5)[C@H]12$

17,17-bis(ethylendioxy)-7-(E)-allyloxyiminoandrostane

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

→

$C=CCO/N=C1\CC2CC(=O)CC[C@]2(C)[C@H]2CC[C@]3(C)C(=O)CC[C@H]3[C@H]12$

title compound

Rendimiento 76.0%

$C=CCO/N=C1\CC2CC(=O)CC[C@]2(C)[C@H]2CC[C@]3(C)C(=O)CC[C@H]3[C@H]12$

7-(E)-Allyloxyiminoandrostane-3,17-dione

Rendimiento 76.0%

Reactantes

$C=CCO/N=C1\CC2CCCC[C@]2(C)[C@H]2CC[C@@]3(C)[C@@H](CC45OCCOC43OCCO5)[C@H]12$

17,17-bis(ethylendioxy)-7-(E)-allyloxyiminoandrostane

6-methyleneandrostane-3,17-dione

Reactivos

Ninguno

Condiciones de reacción

Condiciones detalladas

See reaction.notes.procedure_details.

Tratamiento posterior

1
OtroThe crude product was purified by flash chromatography (SiO2, n-hexane/EtOAc 8/2)

Procedimiento

The title compound II-av was prepared in 76% yield from 3,3:17,17-bis(ethylendioxy)-7-(E)-allyloxyiminoandrostane 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 8/2). 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 5.98 (1H, m), 5.24 (1H, m), 5.14 (1H, m), 4.48 (2H, m), 2.40-1.10 (20H, m), 1.00 (3H, s), 0.81 (3H, s).

Fuente

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