HCID 69133284, compound → 7beta-Hydroxymethylandrostane-3,17-dione

HRID 1912720Notes

Reaction equation

HRID 1912720 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@@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)#N>>[OH:2][CH2:1][C@H:33]1[CH2:32][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]1[C@H:35]1[C@@:39]([CH2:41][CH2:42]2)([CH3:40])[C:38](=[O:52])[CH2:37][CH2:36]1

Participants

3

Reactant 2

HCID 69133284HCID 69133284, compoundHCID 8663558717,17-Bis(ethylendioxy)-7beta-hydroxymethylandrostane

Product 1

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

Procedure

7β-Hydroxymethylandrostane-3,17-dione (II-by) was prepared in 85% yield from 3,3:17,17-bis(ethylendioxy)-7β-hydroxymethylandrostane 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, acetone-d6, ppm from TMS): δ 3.66 (m, 2H), 3.64 (t, 1H), 2.51-0.80 (m, 21H), 1.07 (s, 3H), 0.89 (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-e711a1f4d1fe4672a4f745a86ba8be43
Source dataset
uspto-grants-2013_12
Patent number
US08609644B2

Reaction notes

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