19-Methoxyandrost-4-ene-3,17-dione → 19-Methoxyandrost-5-ene-3,17-dione

HRID 1390761Notes

Reaction equation

HRID 1390761 reaction equation
[CH3:1][O:2][CH2:3][C@@:4]12[C@@H:21]3[C@H:12]([C@H:13]4[C@@:17]([CH2:19][CH2:20]3)([CH3:18])[C:16](=[O:22])[CH2:15][CH2:14]4)[CH2:11][CH2:10][C:9]1=[CH:8][C:7](=[O:23])[CH2:6][CH2:5]2.[CH3:24][O:25][CH2:26][C@@:27]12[C@@H:44]3[C@H:35]([C@H:36]4[C@@:40]([CH2:42][CH2:43]3)([CH3:41])[C:39](=[O:45])[CH2:38][CH2:37]4)[CH2:34][CH2:33][C:32]1=[CH:31][C:30](=[O:46])[CH2:29][C@H:28]2[CH3:47].[CH3:48][O:49][CH2:50][C@@:51]12[C@@H:68]3[C@H:59]([C@H:60]4[C@@:64]([CH2:66][CH2:67]3)([CH3:65])[C:63](=[O:69])[CH2:62][CH2:61]4)[CH2:58][C@H:57]([CH3:70])[C:56]1=[CH:55][C:54](=[O:71])[CH2:53][CH2:52]2>>[CH3:1][O:2][CH2:3][C@@:4]12[C@@H:21]3[C@H:12]([C@H:13]4[C@@:17]([CH2:19][CH2:20]3)([CH3:18])[C:16](=[O:22])[CH2:15][CH2:14]4)[CH2:11][CH:10]=[C:9]1[CH2:8][C:7](=[O:23])[CH2:6][CH2:5]2.[CH3:24][O:25][CH2:26][C@@:27]12[C@@H:44]3[C@H:35]([C@H:36]4[C@@:40]([CH2:42][CH2:43]3)([CH3:41])[C:39](=[O:45])[CH2:38][CH2:37]4)[CH2:34][CH:33]=[C:32]1[CH2:31][C:30](=[O:46])[CH2:29][C@H:28]2[CH3:47].[CH3:48][O:49][CH2:50][C@@:51]12[C@@H:68]3[C@H:59]([C@H:60]4[C@@:64]([CH2:66][CH2:67]3)([CH3:65])[C:63](=[O:69])[CH2:62][CH2:61]4)[CH2:58][C:57]([CH3:70])=[C:56]1[CH2:55][C:54](=[O:71])[CH2:53][CH2:52]2

Participants

6

Reactant 3

HCID 5415304219-Methoxyandrost-4-ene-3,17-dioneHCID 7058596519-Methoxy-6alpha-methyl-4-androstene-3,17-dioneHCID 7058597719-Methoxy-1beta-methyl-4-androstene-3,17-dione

Product 3

HCID 7060491319-Methoxyandrost-5-ene-3,17-dioneHCID 7060567119-Methoxy-1beta-methyl-5-androstene-3,17-dioneHCID 7060597519-Methoxy-6-methyl-5-androsten-3,17-dione

Procedure

Substituting 6α,17α-dimethyl-17β,19-di(trimethylsiloxy)-4-androsten-3-one, 19-methoxyandrost-4-ene-3,17-dione, 19-methoxy-1β-methyl-4-androstene-3,17-dione and 19-methoxy-6α-methyl-4-androstene-3,17-dione for the 17α-propynyl-17β,19-di(trimethylsiloxy)androst-4-en-3-one above results in the formation of 6,17α-dimethyl-17β,19-di(trimethylsiloxy)-5-androsten-3-one, 19-methoxyandrost-5-ene-3,17-dione, 19-methoxy-1β-methyl-5-androstene-3,17-dione and 19-methoxy-6-methyl-5-androstene-3,17-dione, respectively.

Sources & evidence

ORD record
ord-33d8856d4436430ca7750d27b54aa97b
Source dataset
uspto-grants-1979_02
Patent number
US04139617

Reaction notes

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