19-Trimethylsiloxy-4-androstene-3,17-dione → 19-Triphenylsiloxy-5-androstene-3,17-dione

HRID 1390779Notes

Reaction equation

HRID 1390779 reaction equation
[CH3:1][C@H:2]1[C@@:19]2([CH2:20][O:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[C:6]([CH2:7][CH2:8][C@@H:9]3[C@@H:18]2[CH2:17][CH2:16][C@@:14]2([CH3:15])[C@H:10]3[CH2:11][CH2:12][C:13]2=[O:26])=[CH:5][C:4](=[O:27])[CH2:3]1.[CH3:28][C@@H:29]1[C:46]2[C@:41]([CH2:48][O:49][Si:50]([CH3:53])([CH3:52])[CH3:51])([CH2:42][CH2:43][C:44](=[O:47])[CH:45]=2)[C@@H:40]2[C@H:31]([C@H:32]3[C@@:36]([CH2:38][CH2:39]2)([CH3:37])[C:35](=[O:54])[CH2:34][CH2:33]3)[CH2:30]1.[C:55]1([Si:61]([C:90]2[CH:95]=[CH:94][CH:93]=[CH:92][CH:91]=2)([C:84]2[CH:89]=[CH:88][CH:87]=[CH:86][CH:85]=2)[O:62][CH2:63][C@@:64]23[C@@H:81]4[C@H:72]([C@H:73]5[C@@:77]([CH2:79][CH2:80]4)([CH3:78])[C:76](=[O:82])[CH2:75][CH2:74]5)[CH2:71][CH2:70][C:69]2=[CH:68][C:67](=[O:83])[CH2:66][CH2:65]3)[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1.C[Si](C)(C)OC[C@@]12[C@@H]3[C@H]([C@H]4[C@@](CC3)(C)C(=O)CC4)CCC1=CC(=O)CC2>>[CH3:1][C@H:2]1[C@@:19]2([CH2:20][O:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[C:6](=[CH:7][CH2:8][C@@H:9]3[C@@H:18]2[CH2:17][CH2:16][C@@:14]2([CH3:15])[C@H:10]3[CH2:11][CH2:12][C:13]2=[O:26])[CH2:5][C:4](=[O:27])[CH2:3]1.[CH3:28][C:29]1[CH2:30][C@@H:31]2[C@@H:40]([C@:41]3([CH2:48][O:49][Si:50]([CH3:51])([CH3:53])[CH3:52])[C:46]=1[CH2:45][C:44](=[O:47])[CH2:43][CH2:42]3)[CH2:39][CH2:38][C@@:36]1([CH3:37])[C@H:32]2[CH2:33][CH2:34][C:35]1=[O:54].[C:84]1([Si:61]([C:90]2[CH:91]=[CH:92][CH:93]=[CH:94][CH:95]=2)([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[O:62][CH2:63][C@@:64]23[C@@H:81]4[C@H:72]([C@H:73]5[C@@:77]([CH2:79][CH2:80]4)([CH3:78])[C:76](=[O:82])[CH2:75][CH2:74]5)[CH2:71][CH:70]=[C:69]2[CH2:68][C:67](=[O:83])[CH2:66][CH2:65]3)[CH:85]=[CH:86][CH:87]=[CH:88][CH:89]=1

Participants

7

Reactant 4

HCID 2280149719-Trimethylsiloxy-4-androstene-3,17-dioneHCID 2280323919-Triphenylsiloxy-4-androstene-3,17-dioneHCID 228032641beta-Methyl-19-trimethylsiloxy-4-androstene-3,17-dioneHCID 228032726alpha-Methyl-19-trimethylsiloxy-4-androstene-3,17-dione

Product 3

HCID 2280690819-Triphenylsiloxy-5-androstene-3,17-dioneHCID 228069111beta-Methyl-19-trimethylsiloxy-5-androstene-3,17-dioneHCID 228069446-Methyl-19-trimethylsiloxy-5-androstene-3,17-dione

Procedure

Substituting 1β-methyl-19-trimethylsiloxy-4-androstene-3,17-dione, 6α-methyl-19-trimethylsiloxy-4-androstene-3,17-dione and 19-triphenylsiloxy-4-androstene-3,17-dione for the 19-trimethylsiloxy-4-androstene-3,17-dione above results in the preparation of 1β-methyl-19-trimethylsiloxy-5-androstene-3,17-dione, 6-methyl-19-trimethylsiloxy-5-androstene-3,17-dione and 19-triphenylsiloxy-5-androstene-3,17-dione, respectively.

Sources & evidence

ORD record
ord-c8b46310d1a04c07b801b3c16c44e80e
Source dataset
uspto-grants-1979_02
Patent number
US04139617

Reaction notes

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