17,17-Bis(ethylendioxy)-6-methyleneandrostane → 7-Methyleneandrostane-3,17-dione

HRID 1912717Notes

Reaction equation

HRID 1912717 reaction equation
[CH2:1]1COC23OCCOC2([C@]2(CC[C@H]4[C@@H](CC(=C)C5[C@]4(C)CCCC5)[C@@H]2C3)C)O1.C([C@@H:31]1[CH:48]2[C@:43]([CH3:50])([CH2:44][CH2:45][C:46](=[O:49])[CH2:47]2)[C@@H:42]2[C@H:33]([C@H:34]3[C@@:38]([CH2:40][CH2:41]2)([CH3:39])[C:37](=[O:51])[CH2:36][CH2:35]3)[CH2:32]1)#N>>[CH2:1]=[C:32]1[CH2:31][CH:48]2[C@:43]([CH3:50])([CH2:44][CH2:45][C:46](=[O:49])[CH2:47]2)[C@@H:42]2[C@@H:33]1[C@H:34]1[C@@:38]([CH2:40][CH2:41]2)([CH3:39])[C:37](=[O:51])[CH2:36][CH2:35]1

Participants

3

Reactant 2

HCID 6753593917,17-Bis(ethylendioxy)-6-methyleneandrostaneHCID 69133284HCID 69133284, compound

Product 1

HCID 675351097-Methyleneandrostane-3,17-dioneYield 87%

Procedure

The title compound II-bv was prepared in 87% yield from 3,3:17,17-bis(ethylendioxy)-6-methyleneandrostane 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 4.78 (m, 1H), 4.76 (m, 1H), 2.53-0.88 (m, 20H), 1.23 (s, 3H), 0.91 (s, 3H).

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-a08eeaebe7ca416f848891fc1ab7099b
Source dataset
uspto-grants-2013_12
Patent number
US08609644B2

Reaction notes

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