HCID 67536381, compound → (7E,8R,9S,10S,13S,14S)-10,13-dimethyl-7-prop-2-enoxyimino-1,2,4,5,6,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-3,17-dione

HRID 42114Notes

Reaction equation

C1CO[C:8]23OCCO[C:3]2([C@:4]2([CH2:27][CH2:26][C@H:25]4[C@@H:15](/[C:16](=[N:28]/[O:29][CH2:30][CH:31]=[CH2:32])/[CH2:17][CH:18]5[C@:23]4([CH3:24])[CH2:22][CH2:21][CH2:20][CH2:19]5)[C@@H:6]2[CH2:7]3)[CH3:5])[O:2]1.C=C1C2[C@](C)(CCC(=[O:52])C2)[C@@H]2[C@H]([C@H]3[C@@](CC2)(C)C(=O)CC3)C1>>[CH2:30]([O:29]/[N:28]=[C:16]1/[C@@H:15]2[C@@H:25]([C@:23]3([CH3:24])[CH:22]([CH2:17]/1)[CH2:21][C:20](=[O:52])[CH2:19][CH2:18]3)[CH2:26][CH2:27][C@@:4]1([CH3:5])[C@H:6]2[CH2:7][CH2:8][C:3]1=[O:2])[CH:31]=[CH2:32]

Participants

Reactant 2

HCID 67536381HCID 67536381, compound

HCID 178460000HCID 178460000, compound

Product 1

HCID 87655215(7E,8R,9S,10S,13S,14S)-10,13-dimethyl-7-prop-2-enoxyimino-1,2,4,5,6,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-3,17-dioneYield 76%

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-b09563a52f92484382a41836d55413b4
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536160B2

Reaction notes

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