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

HRID 1912694Notes

Reaction equation

HRID 1912694 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]([CH2:16][C@H:17]([NH:28][CH:29]=[O:30])[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:51])C2)[C@@H]2[C@H]([C@H]3[C@@](CC2)(C)C(=O)CC3)C1)#N>>[CH:29]([NH:28][C@@H:17]1[CH:18]2[C@:23]([CH3:24])([CH2:22][CH2:21][C:20](=[O:51])[CH2:19]2)[C@@H:25]2[C@H:15]([C@H:6]3[C@@:4]([CH2:27][CH2:26]2)([CH3:5])[C:3](=[O:12])[CH2:8][CH2:7]3)[CH2:16]1)=[O:30]

Participants

3

Reactant 2

HCID 69133284HCID 69133284, compoundHCID 8663557017,17-Bis(ethylendioxy)-6alpha-formamidoandrostane

Product 1

HCID 866355696alpha-Formamidoandrostane-3,17-dioneYield 96%

Procedure

The title compound II-bc was prepared in 96% yield from 3,3:17,17-bis(ethylendioxy)-6α-formamidoandrostane 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 8.02-7.56 (m, 2H), 3.74 (m, 1H), 2.54-0.70 (m, 20H), 1.04 (s, 3H), 0.80 (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-64642e60f1674d45af75df2fb315c976
Source dataset
uspto-grants-2013_12
Patent number
US08609644B2

Reaction notes

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