19-Hydroxy-1alpha,4alpha-dimethyl-5-androstene-3,17-dione → 4alpha-Methyl-5-androstene-3beta,17beta,19-triol

HRID 1390745Notes

Reaction equation

HRID 1390745 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@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]>>[CH3:23][C@@H:12]1[C@@H:13]([OH:22])[CH2:14][CH2:15][C@@:16]2([CH2:17][OH:18])[C:11]1=[CH:10][CH2:9][C@@H:8]1[C@@H:19]2[CH2:20][CH2:21][C@@:3]2([CH3:4])[C@H:5]1[CH2:6][CH2:7][C@@H:2]2[OH:1].[CH3:47][C@@H:27]1[C@@:26]2([CH2:25][OH:24])[C:31](=[CH:32][CH2:33][C@@H:34]3[C@@H:43]2[CH2:42][CH2:41][C@@:39]2([CH3:40])[C@H:35]3[CH2:36][CH2:37][C@@H:38]2[OH:44])[C@H:30]([CH3:45])[C@@H:29]([OH:46])[CH2:28]1.[CH3:70][C@@H:59]1[C@@H:60]([OH:69])[CH2:61][CH2:62][C@@:63]2([CH2:64][OH:65])[C:58]1=[CH:57][C@@H:56]([CH3:71])[C@@H:55]1[C@@H:66]2[CH2:67][CH2:68][C@@:50]2([CH3:51])[C@H:52]1[CH2:53][CH2:54][C@@H:49]2[OH:48]

Participants

6

Reactant 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

Product 3

HCID 706055374alpha-Methyl-5-androstene-3beta,17beta,19-triolHCID 706057574alpha,7alpha-Dimethyl-5-androstene-3beta,17beta,19-triolHCID 706061051alpha,4alpha-Dimethyl-5-androstene-3beta,17beta,19-triol

Procedure

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

Sources & evidence

ORD record
ord-0874433ad64244f0abd971f047d5c5b2
Source dataset
uspto-grants-1979_02
Patent number
US04139617

Reaction notes

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