HCID 69133284, compound → 6beta-Methoxymethylandrostane-3,17-dione

HRID 1912674Notes

Reaction equation

HRID 1912674 reaction equation
[CH2:1]1COC23OCCOC2([C@]2(CC[C@H]4[C@@H](C[C@@H](COC)C5[C@]4(C)CCCC5)[C@@H]2C3)C)[O:2]1.[C:31]([C@@H:33]1[CH:50]2[C@:45]([CH3:52])([CH2:46][CH2:47][C:48](=[O:51])[CH2:49]2)[C@@H:44]2[C@H:35]([C@H:36]3[C@@:40]([CH2:42][CH2:43]2)([CH3:41])[C:39](=[O:53])[CH2:38][CH2:37]3)[CH2:34]1)#N>>[CH3:1][O:2][CH2:31][C@H:33]1[CH:50]2[C@:45]([CH3:52])([CH2:46][CH2:47][C:48](=[O:51])[CH2:49]2)[C@@H:44]2[C@H:35]([C@H:36]3[C@@:40]([CH2:42][CH2:43]2)([CH3:41])[C:39](=[O:53])[CH2:38][CH2:37]3)[CH2:34]1

Participants

3

Reactant 2

HCID 69133284HCID 69133284, compoundHCID 8665149817,17-Bis(ethylendioxy)-6beta-methoxymethylandrostane

Product 1

HCID 691339676beta-Methoxymethylandrostane-3,17-dioneYield 90%

Procedure

The title compound II-aj was prepared in 90% yield from 3,3:17,17-bis(ethylendioxy)-6β-methoxymethylandrostane 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. The residue was purified by flash chromatography (SiO2, n-hexane/CH2Cl2/acetone 70/10/20). 1H-NMR (300 MHz, acetone-d6, ppm from TMS): δ 3.45 (m, 2H), 3.27 (s, 3H), 2.80-0.80 (m, 21H), 1.10 (s, 3H), 0.89 (s, 3H).

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/CH2Cl2/acetone 70/10/20)

Sources & evidence

ORD record
ord-5838251eb4da40749e7fa205593aa84f
Source dataset
uspto-grants-2013_12
Patent number
US08609644B2

Reaction notes

Loading…