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

HRID 42106Notes

Reaction equation

HRID 42106 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:29]\[O:30][CH3:31])/[C@:18]5([OH:28])[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:51])C2)[C@@H]2[C@H]([C@H]3[C@@](CC2)(C)C(=O)CC3)C1>>[OH:28][C@:18]12[CH2:19][C:20](=[O:51])[CH2:21][CH2:22][C@:23]1([CH3:24])[C@@H:25]1[C@H:15]([C@H:6]3[C@@:4]([CH2:27][CH2:26]1)([CH3:5])[C:3](=[O:2])[CH2:8][CH2:7]3)[CH2:16]/[C:17]/2=[N:29]\[O:30][CH3:31]

Participants

3

Reactant 2

HCID 67536381HCID 67536381, compoundHCID 154041432HCID 154041432, compound

Product 1

HCID 87655454(5R,6E,8R,9S,10R,13S,14S)-5-hydroxy-6-methoxyimino-10,13-dimethyl-2,4,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17-dioneYield 80%

Procedure

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).

Workup

  1. washThe combined organic extracts were washed with H2O
  2. dry with materialdried over Na2SO4
  3. customevaporated to dryness
  4. customThe residue was purified by flash chromatography (SiO2, n-hexane/acetone/CH2Cl2 60/20/20)

Sources & evidence

ORD record
ord-d3988ce5b8ba42909d0a853d2ac79ab5
Source dataset
uspto-grants-2013_09
Patent number
US08536160B2

Reaction notes

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