HCID 69133284, compound → 6alpha-Ethynylandrostane-3,17-dione

HRID 1912693Notes

Reaction equation

HRID 1912693 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@H:17]([C:28]#[CH:29])[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:50])C2)[C@@H]2[C@H]([C@H]3[C@@](CC2)(C)C(=O)CC3)C1)#N>>[C:28]([C@@H:17]1[CH:18]2[C@:23]([CH3:24])([CH2:22][CH2:21][C:20](=[O:50])[CH2:19]2)[C@@H:25]2[C@H:15]([C@H:6]3[C@@:4]([CH2:27][CH2:26]2)([CH3:5])[C:3](=[O:2])[CH2:8][CH2:7]3)[CH2:16]1)#[CH:29]

Participants

3

Reactant 2

HCID 69133284HCID 69133284, compoundHCID 8663557317,17-Bis(ethylendioxy)-6alpha-ethynylandrostane

Product 1

HCID 866355726alpha-Ethynylandrostane-3,17-dioneYield 46%

Procedure

The title compound II-bb was prepared in 46% yield from 3,3:17,17-bis(ethylendioxy)-6α-ethynylandrostane 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, cyclohexane/CH2Cl2/acetone 80/10/10). 1H-NMR (300 MHz, acetone-d6, ppm from TMS): δ 2.69-0.78 (m, 22H), 1.12 (s, 3H), 0.87 (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, cyclohexane/CH2Cl2/acetone 80/10/10)

Sources & evidence

ORD record
ord-2963c9474c41409fa79994648e8ab1eb
Source dataset
uspto-grants-2013_12
Patent number
US08609644B2

Reaction notes

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