HCID 67536381, compound → 7-Methyleneandrostane-3,17-dione

HRID 42116Notes

Reaction equation

HRID 42116 reaction equation
[CH2:1]1COC23OCCOC2([C@]2(CC[C@H]4[C@@H](C(=C)CC5[C@]4(C)CCCC5)[C@@H]2C3)C)O1.C=[C:30]1[CH:47]2[C@:42]([CH3:49])([CH2:43][CH2:44][C:45](=[O:48])[CH2:46]2)[C@@H:41]2[C@H:32]([C@H:33]3[C@@:37]([CH2:39][CH2:40]2)([CH3:38])[C:36](=[O:50])[CH2:35][CH2:34]3)[CH2:31]1>>[CH2:1]=[C:31]1[CH2:30][CH:47]2[C@:42]([CH3:49])([CH2:43][CH2:44][C:45](=[O:48])[CH2:46]2)[C@@H:41]2[C@@H:32]1[C@H:33]1[C@@:37]([CH2:39][CH2:40]2)([CH3:38])[C:36](=[O:50])[CH2:35][CH2:34]1

Participants

3

Reactant 2

HCID 67536381HCID 67536381, compoundHCID 86635586HCID 86635586, compound

Product 1

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

Procedure

The title compound II-aw was prepared in 87% yield from 3,3:17,17-bis(ethylendioxy)-7-methyleneandrostane by the procedure described above for the preparation of 6-methyleneandrostane-3,17-dione (I-ac, Prepn. 13). The combined organic extracts were washed with H2O, dried over Na2SO4 and evaporated to dryness. 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 4.70 (1H, m), 4.62 (1H, m), 2.20-1.10 (20H, m), 1.00 (3H, s), 0.88 (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-107de71278fe451a958a6c889464c541
Source dataset
uspto-grants-2013_09
Patent number
US08536160B2

Reaction notes

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