HCID 69133284, compound → 7alpha-Hydroxyandrostane-3,17-dione

HRID 1912713Notes

Reaction equation

HRID 1912713 reaction equation
C1CO[C:8]23OCC[O:12][C:3]2([C@:4]2([CH2:27][CH2:26][C@H:25]4[C@@H:15]([C@H:16]([OH:28])[CH2:17][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])O1.C([C@@H]1C2[C@](C)(CCC(=[O:49])C2)[C@@H]2[C@H]([C@H]3[C@@](CC2)(C)C(=O)CC3)C1)#N>>[OH:28][C@@H:16]1[CH2:17][CH:18]2[C@:23]([CH3:24])([CH2:22][CH2:21][C:20](=[O:49])[CH2:19]2)[C@@H:25]2[C@@H:15]1[C@H:6]1[C@@:4]([CH2:27][CH2:26]2)([CH3:5])[C:3](=[O:12])[CH2:8][CH2:7]1

Participants

3

Reactant 2

HCID 69133284HCID 69133284, compoundHCID 86635589HCID 86635589, compound

Product 1

HCID 690100697alpha-Hydroxyandrostane-3,17-dioneYield 89%

Procedure

The title compound (II-bt) was prepared in 89% yield from 3,3:17,17-bis(ethylendioxy)-7α-hydroxyandrostane 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 4.34 (d, 1H), 3.75 (m, 1H), 2.50-1.00 (m, 20H), 0.96 (s, 3H), 0.78 (s, 6H).

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-eae9efa8eceb44bfb5c151d1d9efda20
Source dataset
uspto-grants-2013_12
Patent number
US08609644B2

Reaction notes

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