19-Hydroxytestosterone → 17beta,19-Dihydroxy-4-methyl-4-androsten-3-one

HRID 1390743Notes

Reaction equation

HRID 1390743 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]2[C@H:8]3[C@H:19]([CH2:20][CH2:21][C@:3]12[CH3:4])[C@:16]1([CH2:17][OH:18])[C:11](=[CH:12][C:13](=[O:22])[CH2:14][CH2:15]1)[CH2:10][CH2:9]3.[OH:23][CH2:24][C@@:25]12[C@@H:42]3[C@H:33]([C@H:34]4[C@@:38]([CH2:40][CH2:41]3)([CH3:39])[C:37](=[O:43])[CH2:36][CH2:35]4)[CH2:32][CH2:31][C:30]1=[CH:29][C:28](=[O:44])[CH2:27][C@@H:26]2[CH3:45].[OH:46][C@H:47]1[CH2:52][CH2:51][C@H:50]2[C@H:53]3[C@H:64]([CH2:65][CH2:66][C@:48]12[CH3:49])[C@:61]1([CH2:62][OH:63])[C:56](=[CH:57][C:58](=[O:67])[CH2:59][CH2:60]1)[CH2:55][C@H:54]3[CH3:68]>>[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]2[C@H:8]3[C@H:19]([CH2:20][CH2:21][C@:3]12[CH3:4])[C@:16]1([CH2:17][OH:18])[C:11](=[C:12]([CH3:24])[C:13](=[O:22])[CH2:14][CH2:15]1)[CH2:10][CH2:9]3.[OH:23][CH2:24][C@@:25]12[C@@H:42]3[C@H:33]([C@H:34]4[C@@:38]([CH2:40][CH2:41]3)([CH3:39])[C:37](=[O:43])[CH2:36][CH2:35]4)[CH2:32][CH2:31][C:30]1=[C:29]([CH3:47])[C:28](=[O:44])[CH2:27][C@@H:26]2[CH3:45].[OH:46][C@H:47]1[CH2:52][CH2:51][C@H:50]2[C@H:53]3[C@H:64]([CH2:65][CH2:66][C@:48]12[CH3:49])[C@:61]1([CH2:62][OH:63])[C:56](=[C:57]([CH3:2])[C:58](=[O:67])[CH2:59][CH2:60]1)[CH2:55][C@H:54]3[CH3:68]

Participants

6

Reactant 3

HCID 15096819-HydroxytestosteroneHCID 7058400819-Hydroxy1alpha-methyl-4-androstene-3,17-dioneHCID 7058499517beta,19-Dihydroxy-7alpha-methyl-4-androstene-3-one

Product 3

HCID 5364116017beta,19-Dihydroxy-4-methyl-4-androsten-3-oneHCID 5385130017beta,19-Dihydroxy-4,7alpha-dimethyl-4-androsten-3-oneHCID 7058545619-Hydroxy-1alpha,4-dimethyl-4-androstene-3,17-dione

Procedure

Following essentially the same procedure and substituting 17β,19-dihydroxy-4-androsten-3-one, 19-hydroxy-1α-methyl-4-androstene-3,17-dione and 17β,19-dihydroxy-7α-methyl-4-androstene-3-one for the 17β,19-dihydroxy-6α,17α-dimethyl-4-androsten-3-one above results in the preparation of 17β,19-dihydroxy-4-methyl-4-androsten-3-one, 19-hydroxy-1α,4-dimethyl-4-androstene-3,17-dione, and 17β,19-dihydroxy-4,7α-dimethyl-4-androsten-3-one, respectively.

Sources & evidence

ORD record
ord-afec1f03cb994233ac6d06a88d760dca
Source dataset
uspto-grants-1979_02
Patent number
US04139617

Reaction notes

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