HCID 69133284, compound → 6alpha-Formylandrostane-3,17-dione

HRID 1912682Notes

Reaction equation

HRID 1912682 reaction equation
C1COC23OCCOC2([C@]2(CC[C@H]4[C@@H](C[C@H](C=O)C5[C@]4(C)CCCC5)[C@@H]2C3)C)[O:2]1.[C:30]([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>>[CH:30]([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)=[O:2]

Participants

3

Reactant 2

HCID 69133284HCID 69133284, compoundHCID 8663556717,17-Bis(ethylendioxy)-6alpha-formylandrostane

Product 1

HCID 866355666alpha-Formylandrostane-3,17-dioneYield 85%

Procedure

6α-Formylandrostane-3,17-dione was prepared in 85% yield from 3,3:17,17-bis(ethylendioxy)-6α-formylandrostane (Prepn. 11) 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 to give 6α-formylandrostane-3,17-dione. 1H-NMR (300 MHz, acetone-d6, ppm from TMS): δ 9.50 (d, 1H), 2.56-0.82 (m, 21H), 1.16 (s, 3H), 0.88 (s, 3H).

Workup

  1. washThe combined organic extracts were washed with H2O
  2. dry with materialdried over Na2SO4
  3. customevaporated to dryness
  4. customto give 6α-formylandrostane-3,17-dione

Sources & evidence

ORD record
ord-516878947eb84ac3851258c1e5aae549
Source dataset
uspto-grants-2013_12
Patent number
US08609644B2

Reaction notes

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