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

HRID 1912689Notes

Reaction equation

HRID 1912689 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]\[O:29][CH2:30][CH3:31])/[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([C@@H]1C2[C@](C)(CCC(=[O:52])C2)[C@@H]2[C@H]([C@H]3[C@@](CC2)(C)C(=O)CC3)C1)#N>>[CH2:30]([O: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:52])[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])[CH3:31]

Participants

3

Reactant 2

HCID 69133284HCID 69133284, compoundHCID 178474300(E,2S,5S,6R,14R,15S)-N-ethoxy-2,6-dimethyl-18,21,22,25-tetraoxahexacyclo[15.4.4.01,17.02,15.05,14.06,11]pentacosan-12-imine

Product 1

HCID 87709931(6E,8R,9S,10R,13S,14S)-6-ethoxyimino-10,13-dimethyl-1,2,4,5,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-3,17-dioneYield 100%

Procedure

The title compound II-av was prepared in 100% yield from 3,3:17,17-bis(ethylendioxy)-6(E)-ethoxyiminoandrostane by the procedure described above for the preparation of 6α-cyanoandrostane-3,17-dione (II-ac, Prepn. 3). The combined organic extracts were washed with H2O, dried over Na2SO4 and evaporated to dryness. 1H-NMR (300 MHz, acetone-d6, ppm from TMS): δ 4.03 (2H, q), 3.40 (1H, dd), 2.70-1.12 (19H, m), 1.20 (3H, t), 1.01 (3H, s), 0.87 (3H, s).

Workup

  1. washThe combined organic extracts were washed with H2O
  2. dry with materialdried over Na2SO4
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-9dee7afe7da3497689687a0d33ea9e72
Source dataset
uspto-grants-2013_12
Patent number
US08609644B2

Reaction notes

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