HCID 69133284, compound → (7E,8R,9S,10S,13S,14S)-7-hydroxyimino-10,13-dimethyl-1,2,4,5,6,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-3,17-dione

HRID 1912711Notes

Reaction equation

HRID 1912711 reaction equation
C1CO[C:8]23OCC[O:12][C:3]2([C@:4]2([CH2:27][CH2:26][C@H:25]4[C@@H:15](/[C:16](=[N:28]/[OH:29])/[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])O1.C([C@@H]1C2[C@](C)(CCC(=[O:50])C2)[C@@H]2[C@H]([C@H]3[C@@](CC2)(C)C(=O)CC3)C1)#N>>[OH:29]/[N:28]=[C:16]1/[C@@H:15]2[C@@H:25]([C@:23]3([CH3:24])[CH:18]([CH2:17]/1)[CH2:19][C:20](=[O:50])[CH2:21][CH2:22]3)[CH2:26][CH2:27][C@@:4]1([CH3:5])[C@H:6]2[CH2:7][CH2:8][C:3]1=[O:12]

Participants

3

Reactant 2

HCID 69133284HCID 69133284, compoundHCID 178421203HCID 178421203, compound

Product 1

HCID 87200828(7E,8R,9S,10S,13S,14S)-7-hydroxyimino-10,13-dimethyl-1,2,4,5,6,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-3,17-dioneYield 50%

Procedure

The title compound II-bq was prepared in 50% yield from 3,3:17,17-bis(ethylendioxy)-7(E)-hydroxyiminoandrostane by the procedure described above for the preparation of 6α-cyanoandrostane-3,17-dione (II-ac, Prepn. 3). The crude product was purified by flash chromatography (SiO2, n-hexane/EtOAc 6/4). 1H-NMR (300 MHz, DMSO-d6, ppm from TMS: δ 10.37 (s, 1H), 2.99 (m, 1H), 2.58-0.67 (m, 19H), 1.12 (s, 3H), 0.82 (s, 3H).

Workup

  1. customThe crude product was purified by flash chromatography (SiO2, n-hexane/EtOAc 6/4)

Sources & evidence

ORD record
ord-3f1d9ddac4d84360b9761f54b7de516a
Source dataset
uspto-grants-2013_12
Patent number
US08609644B2

Reaction notes

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