7alpha-Methyl-1beta,2beta-methylene-4-androstene-3,17-dione → 1beta,7alpha-Dimethyl-4-androstene-3,17-dione

HRID 2397989Notes

Reaction equation

HRID 2397989 reaction equation
[CH3:1][C@@H:2]1[CH2:19][C:18]2[C@:13]([CH3:22])([C@@H:14]3[CH2:21][C@@H:15]3[C:16](=[O:20])[CH:17]=2)[C@@H:12]2[C@@H:3]1[C@H:4]1[C@@:8]([CH2:10][CH2:11]2)([CH3:9])[C:7](=[O:23])[CH2:6][CH2:5]1.[CH3:24][C@@H:25]1[C:42]2[C@:37]([CH3:45])([C@@H:38]3[CH2:44][C@@H:39]3[C:40](=[O:43])[CH:41]=2)[C@@H:36]2[C@H:27]([C@H:28]3[C@@:32]([CH2:34][CH2:35]2)([CH3:33])[C:31](=[O:46])[CH2:30][CH2:29]3)[CH2:26]1.C1[C@@H]2C(=O)C=C3[C@](C)([C@H]12)[C@@H]1[C@H]([C@H]2[C@@](CC1)(C)C(=O)CC2)CC3>>[CH3:21][C@H:14]1[C@@:13]2([CH3:22])[C:18]([CH2:19][C@@H:2]([CH3:1])[C@@H:3]3[C@@H:12]2[CH2:11][CH2:10][C@@:8]2([CH3:9])[C@H:4]3[CH2:5][CH2:6][C:7]2=[O:23])=[CH:17][C:16](=[O:20])[CH2:15]1.[CH3:44][C@H:38]1[C@@:37]2([CH3:45])[C:42]([C@@H:25]([CH3:24])[CH2:26][C@@H:27]3[C@@H:36]2[CH2:35][CH2:34][C@@:32]2([CH3:33])[C@H:28]3[CH2:29][CH2:30][C:31]2=[O:46])=[CH:41][C:40](=[O:43])[CH2:39]1

Participants

5

Reactant 3

HCID 143061247alpha-Methyl-1beta,2beta-methylene-4-androstene-3,17-dioneHCID 542623781beta,2beta-Methylene-4-androstene-3,17-dioneHCID 706143876alpha-Methyl-1beta,2beta-methylene-4-androstene-3,17-dione

Product 2

HCID 537937561beta,7alpha-Dimethyl-4-androstene-3,17-dioneHCID 544335181beta,6alpha-Dimethyl-4-androstene-3,17-dione

Procedure

Substituting 7α-methyl-1β,2β-methylene-4-androstene-3,17-dione and 6α-methyl-1β,2β-methylene-4-androstene-3,17-dione for the 1β,2β-methylene-4-androstene-3,17-dione above results in the preparation of 1β,7α-dimethyl-4-androstene-3,17-dione and 1β,6α-dimethyl-4-androstene-3,17-dione, respectively.

Sources & evidence

ORD record
ord-6abb03cc43e140498082dca8411c09d8
Source dataset
uspto-grants-1977_05
Patent number
US04022769

Reaction notes

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