17beta,19-Dihydroxy-1alphamethyl-4-androsten-3-one → 17beta,19-Dihydroxy-1alpha,6-dimethyl-5-androsten-3-one

HRID 1390733Notes

Reaction equation

HRID 1390733 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:23])[CH2:14][C@@H:15]1[CH3:22])[C@@H:10]([CH3:24])[CH2:9]3.[OH:25][CH2:26][C@@:27]12[C@@H:44]3[C@H:35]([C@H:36]4[C@@:40]([CH2:42][CH2:43]3)([CH3:41])[C:39](=[O:45])[CH2:38][CH2:37]4)[CH2:34][CH2:33][C:32]1=[CH:31][C:30](=[O:46])[CH2:29][C@@H:28]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](=[CH:59][C:60](=[O:70])[CH2:61][C@@H:62]1[CH3:69])[CH2:57][C@H:56]3[CH3:71].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>>[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]([CH2:12][C:13](=[O:23])[CH2:14][C@@H:15]1[CH3:22])=[C:10]([CH3:24])[CH2:9]3.[OH:25][CH2:26][C@@:27]12[C@@H:44]3[C@H:35]([C@H:36]4[C@@:40]([CH2:42][CH2:43]3)([CH3:41])[C:39](=[O:45])[CH2:38][CH2:37]4)[CH2:34][CH:33]=[C:32]1[CH2:31][C:30](=[O:46])[CH2:29][C@@H:28]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]([CH2:59][C:60](=[O:70])[CH2:61][C@@H:62]1[CH3:69])=[CH:57][C@H:56]3[CH3:71]

Participants

7

Reactant 4

HCID 2279742517beta,19-Dihydroxy-1alphamethyl-4-androsten-3-oneHCID 7058393717beta,19-Dihydroxy-1alpha,6alpha-dimethyl-4-androsten-3-oneHCID 7058400819-Hydroxy1alpha-methyl-4-androstene-3,17-dioneHCID 7058545317beta,19-Dihydroxy-1alpha,7alpha-dimethyl-4-androsten-3-one

Product 3

HCID 7060482217beta,19-Dihydroxy-1alpha,6-dimethyl-5-androsten-3-oneHCID 7060500817beta,19-Dihydroxy-1alpha,7alpha-dimethyl-5-androsten-3-oneHCID 7060533419-Hydroxy-1alpha-methyl-5-androstene-3,17-dione

Procedure

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

Sources & evidence

ORD record
ord-7756501679194835b343afae7f43c662
Source dataset
uspto-grants-1979_02
Patent number
US04139617

Reaction notes

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