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

HRID 2397987Notes

Reaction equation

HRID 2397987 reaction equation
[CH3:1][C@@H:2]1[CH2:19][C:18]2[C@:13]([CH3:21])([CH:14]=[CH:15][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:22])[CH2:6][CH2:5]1.[CH3:23][C@@H:24]1[C:41]2[C@:36]([CH3:43])([CH:37]=[CH:38][C:39](=[O:42])[CH:40]=2)[C@@H:35]2[C@H:26]([C@H:27]3[C@@:31]([CH2:33][CH2:34]2)([CH3:32])[C:30](=[O:44])[CH2:29][CH2:28]3)[CH2:25]1.[CH3:45][C@]12CC[C@H]3[C@@H](CCC4[C@]3(C)C=CC(=O)C=4)[C@@H]1CCC2=O>>[CH3:1][C@@H:2]1[CH2:19][C:18]2[C@:13]([CH3:21])([C@@H:14]3[CH2:23][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:22])[CH2:6][CH2:5]1.[CH3:23][C@@H:24]1[C:41]2[C@:36]([CH3:43])([C@@H:37]3[CH2:45][C@@H:38]3[C:39](=[O:42])[CH:40]=2)[C@@H:35]2[C@H:26]([C@H:27]3[C@@:31]([CH2:33][CH2:34]2)([CH3:32])[C:30](=[O:44])[CH2:29][CH2:28]3)[CH2:25]1

Participants

5

Reactant 3

HCID 13472Androsta-1,4-diene-3,17-dioneHCID 104943366alpha-Methyl-1,4-androstadiene-3,17-dioneHCID 540647457alpha-Methyl-1,4-androstadiene-3,17-dione

Product 2

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

Procedure

Following essentially the same procedure and substituting 7α-methyl-1,4-androstadiene-3,17-dione and 6α-methyl-1,4-androstadiene-3,17-dione for the 1,4-androstadiene-3,17-dione above results in the preparation of 7α-methyl-1β,2β-methylene-4-androstene-3,17-dione and 6α-methyl-1β,2β-methylene-4-androstene-3,17-dione.

Sources & evidence

ORD record
ord-26a26ecc457945f1b44c8edb50ace76e
Source dataset
uspto-grants-1977_05
Patent number
US04022769

Reaction notes

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