17beta,19-Dihydroxy-4-methyl-4-androsten-3-one → 19-Hydroxy-1alpha,4alpha-dimethyl-5-androstene-3,17-dione

HRID 1390744Notes

Reaction equation

HRID 1390744 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](=[C:12]([CH3:23])[C:13](=[O:22])[CH2:14][CH2:15]1)[CH2:10][CH2:9]3.[OH:24][CH2:25][C@@:26]12[C@@H:43]3[C@H:34]([C@H:35]4[C@@:39]([CH2:41][CH2:42]3)([CH3:40])[C:38](=[O:44])[CH2:37][CH2:36]4)[CH2:33][CH2:32][C:31]1=[C:30]([CH3:45])[C:29](=[O:46])[CH2:28][C@@H:27]2[CH3:47].[OH:48][C@H:49]1[CH2:54][CH2:53][C@H:52]2[C@H:55]3[C@H:66]([CH2:67][CH2:68][C@:50]12[CH3:51])[C@:63]1([CH2:64][OH:65])[C:58](=[C:59]([CH3:70])[C:60](=[O:69])[CH2:61][CH2:62]1)[CH2:57][C@H:56]3[CH3:71]>>[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@H:12]([CH3:23])[C:13](=[O:22])[CH2:14][CH2:15]1)=[CH:10][CH2:9]3.[OH:24][CH2:25][C@@:26]12[C@@H:43]3[C@H:34]([C@H:35]4[C@@:39]([CH2:41][CH2:42]3)([CH3:40])[C:38](=[O:44])[CH2:37][CH2:36]4)[CH2:33][CH:32]=[C:31]1[C@H:30]([CH3:45])[C:29](=[O:46])[CH2:28][C@@H:27]2[CH3:47].[OH:48][C@H:49]1[CH2:54][CH2:53][C@H:52]2[C@H:55]3[C@H:66]([CH2:67][CH2:68][C@:50]12[CH3:51])[C@:63]1([CH2:64][OH:65])[C:58]([C@H:59]([CH3:70])[C:60](=[O:69])[CH2:61][CH2:62]1)=[CH:57][C@H:56]3[CH3:71]

Participants

6

Reactant 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

Product 3

HCID 7060533319-Hydroxy-1alpha,4alpha-dimethyl-5-androstene-3,17-dioneHCID 7060575617beta,19-Dihydroxy-4alpha-methyl-5-androsten-3-oneHCID 7060585417beta,19-Dihydroxy-4alpha,7alpha-dimethyl-5-androsten-3-one

Procedure

Substituting 17β,19-dihydroxy-4-methyl-4-androsten-3-one, 19-hydroxy-1α,4-dimethyl-4-androstene-3,17-dione, 17β,19-dihydroxy-4,7α-dimethyl-4-androsten-3-one, 4-methyl-17β,19-di(2'-tetrahydropyranyloxy)-4-androsten-3-one and 1α,4-dimethyl-19-(2'-tetrahydropyranyloxy)-4-androstene-3,17-dione for the 17β,19-dihydroxy-4,6α,17α-trimethyl-4-androsten-3-one above results in the formation of 17β,19-dihydroxy-4α-methyl-5-androsten-3-one, 19-hydroxy-1α,4α-dimethyl-5-androstene-3,17-dione, 17β,19-dihydroxy-4α,7α-dimethyl-5-androsten-3-one, 4α-methyl-17β,19-di(2'-tetrahydropyranyloxy)-5-androsten-3-one and 1α,4α-dimethyl-19-(2'-tetrahydropyranyloxy)-5-androstene-3,17-dione, respectively.

Sources & evidence

ORD record
ord-3e426947b3ad4336905770d6812e941a
Source dataset
uspto-grants-1979_02
Patent number
US04139617

Reaction notes

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