HCID 67536381, compound → 6alpha-(2-Hydroxyethyl)androstane-3,17-dione

HRID 42099Notes

Reaction equation

HRID 42099 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.[CH2:31]=[C:32]1[CH:49]2[C@:44]([CH3:51])([CH2:45][CH2:46][C:47](=[O:50])[CH2:48]2)[C@@H:43]2[C@H:34]([C@H:35]3[C@@:39]([CH2:41][CH2:42]2)([CH3:40])[C:38](=[O:52])[CH2:37][CH2:36]3)[CH2:33]1>>[OH:2][CH2:1][CH2:31][C@@H:32]1[CH:49]2[C@:44]([CH3:51])([CH2:45][CH2:46][C:47](=[O:50])[CH2:48]2)[C@@H:43]2[C@H:34]([C@H:35]3[C@@:39]([CH2:41][CH2:42]2)([CH3:40])[C:38](=[O:52])[CH2:37][CH2:36]3)[CH2:33]1

Participants

3

Reactant 2

HCID 67536381HCID 67536381, 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-an 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 6-methyleneandrostane-3,17-dione (II-ac, Prepn. 13). 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 (1H, t), 3.39 (2H, m), 2.46-0.54 (23H, m), 0.98 (3H, s), 0.79 (3H, s).

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-6012c71efd5f4cdc8f783e34136871cf
Source dataset
uspto-grants-2013_09
Patent number
US08536160B2

Reaction notes

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