HCID 67536381, compound → 7beta-Hydroxymethylandrostane-3,17-dione

HRID 42119Notes

Reaction equation

HRID 42119 reaction equation
[CH2:1]1COC23OCCOC2([C@]2(CC[C@H]4[C@@H]([C@@H](CO)CC5[C@]4(C)CCCC5)[C@@H]2C3)C)[O:2]1.C=[C:31]1[CH:48]2[C@:43]([CH3:50])([CH2:44][CH2:45][C:46](=[O:49])[CH2:47]2)[C@@H:42]2[C@H:33]([C@H:34]3[C@@:38]([CH2:40][CH2:41]2)([CH3:39])[C:37](=[O:51])[CH2:36][CH2:35]3)[CH2:32]1>>[OH:2][CH2:1][C@H:32]1[CH2:31][CH:48]2[C@:43]([CH3:50])([CH2:44][CH2:45][C:46](=[O:49])[CH2:47]2)[C@@H:42]2[C@@H:33]1[C@H:34]1[C@@:38]([CH2:40][CH2:41]2)([CH3:39])[C:37](=[O:51])[CH2:36][CH2:35]1

Participants

3

Reactant 2

HCID 67536381HCID 67536381, compoundHCID 8663558717,17-Bis(ethylendioxy)-7beta-hydroxymethylandrostane

Product 1

HCID 690126687beta-Hydroxymethylandrostane-3,17-dioneYield 85%

Procedure

7β-Hydroxymethylandrostane-3,17-dione II-aw was prepared in 85% yield from 3,3:17,17-bis(ethylendioxy)-7β-hydroxymethylandrostane 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, acetone-d6, ppm from TMS): δ 3.70-3.60 (2H, m), 3.54 (1H, t), 2.50-0.90 (21H, m), 1.06 (3H, s), 0.86 (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-946de5430cce47c883e7a2656467b201
Source dataset
uspto-grants-2013_09
Patent number
US08536160B2

Reaction notes

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