Reaktion #70384

ord-d3988ce5b8ba42909d0a853d2ac79ab5

Reaktionsgleichung

$CO/N=C1\C[C@H]2[C@@H]3CC45OCCOC4(OCCO5)[C@@]3(C)CC[C@@H]2[C@@]2(C)CCCC[C@]12O$

17,17-bis(ethylendioxy)-5α-hydroxy-6-(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

→

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

title compound

Ausbeute 80.0%

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

5α-Hydroxy-6-(E)-methoxyiminoandrostane-3,17-dione

Ausbeute 80.0%

Edukte

$CO/N=C1\C[C@H]2[C@@H]3CC45OCCOC4(OCCO5)[C@@]3(C)CC[C@@H]2[C@@]2(C)CCCC[C@]12O$

17,17-bis(ethylendioxy)-5α-hydroxy-6-(E)-methoxyiminoandrostane

6-methyleneandrostane-3,17-dione

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen

See reaction.notes.procedure_details.

Aufarbeitung

1
WaschenThe combined organic extracts were washed with H2O
2
Trocknendried over Na2SO4
3
Sonstigeevaporated to dryness
4
SonstigeThe residue was purified by flash chromatography (SiO2, n-hexane/acetone/CH2Cl2 60/20/20)

Vorschrift

The title compound II-ar was prepared in 80% yield from 3,3:17,17-bis(ethylendioxy)-5α-hydroxy-6-(E)-methoxyiminoandrostane 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 over Na2SO4 and evaporated to dryness. The residue was purified by flash chromatography (SiO2, n-hexane/acetone/CH2Cl2 60/20/20). 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 5.46 (1H, s), 3.75 (3H, s), 3.20-2.93 (1H, dd), 2.86-2.75 (1H, d), 2.30-1.10 (17H, m), 0.96 (3H, s), 0.77 (3H, s).

Quelle

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