19-Hydroxyandrostenedione → 4-Methyl-4,6-androstadiene-3,17,19-trione

HRID 1733112

Reaction equation

HRID 1733112 reaction equation
[OH:1][CH2:2][C@@:3]12[C@@H:20]3[C@H:11]([C@H:12]4[C@@:16]([CH2:18][CH2:19]3)([CH3:17])[C:15](=[O:21])[CH2:14][CH2:13]4)[CH2:10][CH2:9][C:8]1=[C:7]([CH3:22])[C:6](=[O:23])[CH2:5][CH2:4]2.[OH:24][C@@:25]1([CH3:46])[CH2:30][CH2:29][C@H:28]2[C@H:31]3[C@H:42]([CH2:43][CH2:44][C@:26]12[CH3:27])[C@:39]1([CH2:40][OH:41])[C:34](=[CH:35][C:36](=[O:45])[CH2:37][CH2:38]1)[CH2:33][CH2:32]3.[OH:47][C@@:48]1([C:69]#[C:70][CH3:71])[CH2:53][CH2:52][C@H:51]2[C@H:54]3[C@H:65]([CH2:66][CH2:67][C@:49]12[CH3:50])[C@:62]1([CH2:63][OH:64])[C:57](=[CH:58][C:59](=[O:68])[CH2:60][CH2:61]1)[CH2:56][CH2:55]3.OC[C@@]12[C@@H]3[C@H]([C@H]4[C@@](CC3)(C)C(=O)CC4)CCC1=CC(=O)CC2>>[CH3:22][C:7]1[C:6](=[O:23])[CH2:5][CH2:4][C@@:3]2([CH:2]=[O:1])[C:8]=1[CH:9]=[CH:10][C@@H:11]1[C@@H:20]2[CH2:19][CH2:18][C@@:16]2([CH3:17])[C@H:12]1[CH2:13][CH2:14][C:15]2=[O:21].[OH:24][C@@:25]1([CH3:46])[CH2:30][CH2:29][C@H:28]2[C@H:31]3[C@H:42]([CH2:43][CH2:44][C@:26]12[CH3:27])[C@:39]1([CH:40]=[O:41])[C:34](=[CH:35][C:36](=[O:45])[CH2:37][CH2:38]1)[CH:33]=[CH:32]3.[OH:47][C@@:48]1([C:69]#[C:70][CH3:71])[CH2:53][CH2:52][C@H:51]2[C@H:54]3[C@H:65]([CH2:66][CH2:67][C@:49]12[CH3:50])[C@:62]1([CH:63]=[O:64])[C:57](=[CH:58][C:59](=[O:68])[CH2:60][CH2:61]1)[CH:56]=[CH:55]3

Participants

7

Reactant 4

HCID 25237919-HydroxyandrostenedioneHCID 5379505019-Hydroxy-4-methyl-4-androstene-3,17-dioneHCID 7058325817beta,19-Dihydroxy-17alpha-methyl-4-androsten-3-oneHCID 7058384317beta,19-Dihydroxy-17alpha-propinyl-4-androsten-3-one

Product 3

HCID 537200574-Methyl-4,6-androstadiene-3,17,19-trioneHCID 8673569317beta-Hydroxy-17alpha-methyl-4,6-androstadiene-3,19-dioneHCID 13171109617beta-Hydroxy-17alpha-propinyl-4,6-androstadiene-3,19-dione

Procedure

Following essentially the same procedure and substituting 19-hydroxy-4-methyl-4-androstene-3,17-dione, 17β,19-dihydroxy-17α-methyl-4-androsten-3-one and 17β,19-dihydroxy-17α-propinyl-4-androsten-3-one for the 19-hydroxy-4-androstene-3,17-dione above results in the preparation of 4-methyl-4,6-androstadiene-3,17,19-trione, 17β-hydroxy-17α-methyl-4,6-androstadiene-3,19-dione and 17β-hydroxy-17α-propinyl-4,6-androstadiene-3,19-dione.

Sources & evidence

ORD record
ord-6ee6896992114d1c966527dd1f25af9d
Source dataset
uspto-grants-1980_12
Patent number
US04239681

Linked notes

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