17beta,19-Dihydroxy-1alphamethyl-4-androsten-3-one → 1alpha,7alpha-Dimethyl-4-androstene-3,17,19-trione

HRID 1834912Notes

Reaction equation

HRID 1834912 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=[CH:7][C:6](=[O:22])[CH2:5][C@@H:4]2[CH3:23].[OH:24][C@H:25]1[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:46])[CH2:37][C@@H:38]1[CH3:45])[CH2:33][C@H:32]3[CH3:47].O[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@]12C)[C@]1(CO)C(=CC(=O)C[C@@H]1C)CC3>>[CH3:23][C@@H:4]1[C@@:3]2([CH:2]=[O:1])[C:8]([CH2:9][CH2:10][C@@H:11]3[C@@H:20]2[CH2:19][CH2:18][C@@:16]2([CH3:17])[C@H:12]3[CH2:13][CH2:14][C:15]2=[O:21])=[CH:7][C:6](=[O:22])[CH2:5]1.[CH3:45][C@@H:38]1[C@@:39]2([CH:40]=[O:41])[C:34]([CH2:33][C@@H:32]([CH3:47])[C@@H:31]3[C@@H:42]2[CH2:43][CH2:44][C@@:26]2([CH3:27])[C@H:28]3[CH2:29][CH2:30][C:25]2=[O:24])=[CH:35][C:36](=[O:46])[CH2:37]1

Participants

5

Reactant 3

HCID 2279742517beta,19-Dihydroxy-1alphamethyl-4-androsten-3-oneHCID 7058400819-Hydroxy1alpha-methyl-4-androstene-3,17-dioneHCID 7058545317beta,19-Dihydroxy-1alpha,7alpha-dimethyl-4-androsten-3-one

Product 2

HCID 538793401alpha,7alpha-Dimethyl-4-androstene-3,17,19-trioneHCID 543865421alpha-Methyl-4-androstene-3,17,19-trione

Procedure

Substituting 17β,19-dihydroxy-1α,17α-dimethyl-4-androsten- 3-one, 19-hydroxy-1α-methyl-4-androstene-3,17-dione, 17β,19-dihydroxy-1α,7α-dimethyl-4-androsten-3-one and 17β,19-dihydroxy-1α,6α,17α-trimethyl-4-androsten-3-one for the 17β,19-dihydroxy-1α-methyl-4-androsten-3-one above results in the preparation of 17β-hydroxy-1α,17α-dimethyl-4-androstene-3,19-dione, 1α- methyl-4-androstene-3,17,19-trione, 1α,7α-dimethyl-4-androstene-3,17,19-trione and 17β-hydroxy-1α,6α,17α-trimethyl-4-androstene-3,19-dione, respectively.

Sources & evidence

ORD record
ord-1dcc992bf0ec41f2bd3028666422fe8a
Source dataset
uspto-grants-1978_01
Patent number
US04071624

Reaction notes

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