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

HRID 42092Notes

Reaction equation

HRID 42092 reaction equation
C1CO[C:8]23OCCO[C:3]2([C@:4]2([CH2:27][CH2:26][C@H:25]4[C@@H:15]([CH2:16]/[C:17](=[N:28]\[OH:29])/[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:49])C2)[C@@H]2[C@H]([C@H]3[C@@](CC2)(C)C(=O)CC3)C1>>[OH:29]/[N:28]=[C:17]1\[CH2:16][C@@H:15]2[C@@H:25]([C@:23]3([CH3:24])[CH:18]\1[CH2:19][C:20](=[O:49])[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:2]

Participants

3

Reactant 2

HCID 67536381HCID 67536381, compoundHCID 178421204(NE)-N-[(2S,5S,6R,14R,15S)-2,6-dimethyl-18,21,22,25-tetraoxahexacyclo[15.4.4.01,17.02,15.05,14.06,11]pentacosan-12-ylidene]hydroxylamine

Product 1

HCID 87653583(6E,8R,9S,10R,13S,14S)-6-hydroxyimino-10,13-dimethyl-1,2,4,5,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-3,17-dioneYield 70%

Procedure

The title compound II-ah was prepared in 70% yield from 3,3:17,17-bis(ethylendioxy)-6-(E)-hydroxyiminoandrostane 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 and evaporated to dryness. The residue was purified by flash chromatography (SiO2, n-hexane/acetone 70/30). 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 10.61 (1H, s), 3.29 (1H, dd), 2.61-1.03 (19H, m), 0.88 (3H, s), 0.79 (3H, s).

Workup

  1. washThe combined organic extracts were washed with H2O
  2. customdried
  3. customevaporated to dryness
  4. customThe residue was purified by flash chromatography (SiO2, n-hexane/acetone 70/30)

Sources & evidence

ORD record
ord-c75a8bd2bdce4099a50b6c51e50435ab
Source dataset
uspto-grants-2013_09
Patent number
US08536160B2

Reaction notes

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