HCID 69133284, compound → 6alpha-(2-Hydroxyethyl)androstane-3,17-dione

HRID 1912678Notes

Reaction equation

HRID 1912678 reaction equation
[CH2:1]1COC23OCCOC2([C@]2(CC[C@H]4[C@@H](C[C@H](CCO)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>>[OH:2][CH2:1][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 8663557517,17-Bis(ethylendioxy)-6alpha-(2-hydroxyethyl)androstane

Product 1

HCID 690106776alpha-(2-Hydroxyethyl)androstane-3,17-dioneYield 100%

Procedure

The title compound II-al was prepared in 100% yield from 3,3:17,17-bis(ethylendioxy)-6α-(2-hydroxyethyl)androstane 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, dmso-d6, ppm from TMS): δ 4.32 (t, 1H), 3.39 (m, 2H), 2.46-0.54 (m, 23H), 0.98 (s, 3H), 0.79 (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-d31c6ba2bda7489c8ad6297d744c352a
Source dataset
uspto-grants-2013_12
Patent number
US08609644B2

Reaction notes

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