HCID 67536381, compound → HCID 67535465, compound

HRID 42103Notes

Reaction equation

HRID 42103 reaction equation
C1COC23OCCOC2([C@]2(CC[C@H]4[C@@H](CC(=C)[C@]5(O)[C@]4(C)CCCC5)[C@@H]2C3)C)[O:2]1.[CH2:30]=[C: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>>[OH:2][C@:48]12[CH2:47][C:46](=[O:49])[CH2:45][CH2:44][C@:43]1([CH3:50])[C@@H:42]1[C@H:33]([C@H:34]3[C@@:38]([CH2:40][CH2:41]1)([CH3:39])[C:37](=[O:51])[CH2:36][CH2:35]3)[CH2:32][C:31]2=[CH2:30]

Participants

3

Reactant 2

HCID 67536381HCID 67536381, compoundHCID 8665150917,17-Bis(ethylendioxy)-5alpha-hydroxy-6-methyleneandrostane

Product 1

HCID 67535465HCID 67535465, compoundYield 85%

Procedure

The title compound II-ap was prepared in 85% yield from 3,3:17,17-bis(ethylendioxy)-5α-hydroxy-6-methyleneandrostane 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/AcOEt 60/40). 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 4.91 (1H, s), 4.81 (1H, bs), 4.58 (1H, bs), 2.82 (1H, d), 2.42-1.10 (17H, m), 0.94 (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/AcOEt 60/40)

Sources & evidence

ORD record
ord-8e53712c9ea149c78a89e6cc6589df87
Source dataset
uspto-grants-2013_09
Patent number
US08536160B2

Reaction notes

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