HCID 69133284, compound → 5alpha-Hydroxy-6beta-cyanoandrostane-3,17-dione

HRID 1912668Notes

Reaction equation

HRID 1912668 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]([C:29]#[N:30])[C@:18]5([OH:28])[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>>[OH:28][C@:18]12[CH2:19][C:20](=[O:51])[CH2:21][CH2:22][C@:23]1([CH3:24])[C@@H:25]1[C@H:15]([C@H:6]3[C@@:4]([CH2:27][CH2:26]1)([CH3:5])[C:3](=[O:12])[CH2:8][CH2:7]3)[CH2:16][C@H:17]2[C:29]#[N:30]

Participants

3

Reactant 2

HCID 69133284HCID 69133284, compoundHCID 8665149617,17-Bis(ethylendioxy)-5alpha-hydroxy-6beta-cyanoandrostane

Product 1

HCID 698111025alpha-Hydroxy-6beta-cyanoandrostane-3,17-dioneYield 82%

Procedure

The title compound II-ai was prepared in 82% yield from 3,3:17,17-bis(ethylendioxy)-5α-hydroxy-6β-cyanoandrostane by the procedure described above for the preparation of 6α-cyanoandrostane-3,17-dione (II-ac, Prepn. 3). The crude product was purified by flash chromatography (SiO2, n-hexane/CH2Cl2/acetone 60/20/20) to give the title compound II-ae. 1H-NMR (300 MHz, acetone-d6, ppm from TMS): δ 4.27 (s, 1H), 3.21 (d, 1H), 2.92 (m, 1H), 2.62-1.24 (m, 18H), 1.50 (s, 3H), 0.93 (s, 3H).

Workup

  1. customThe crude product was purified by flash chromatography (SiO2, n-hexane/CH2Cl2/acetone 60/20/20)
  2. customto give the title compound II-ae

Sources & evidence

ORD record
ord-75656ea3c56e4461847676558f4d3a13
Source dataset
uspto-grants-2013_12
Patent number
US08609644B2

Reaction notes

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