19-Methoxyandrost-4-ene-3,17-dione → 19-Methoxy-6alpha-methyl-4-androstene-3,17-dione

HRID 1733074Notes

Reaction equation

HRID 1733074 reaction equation
[OH:1][CH2:2][C@@:3]12[C@@H:20]3[C@H:11]([C@H:12]4[C@@:16]([CH2:18][CH2:19]3)([CH3:17])[C:15](=[O:21])[CH2:14][CH2:13]4)[CH2:10][CH2:9][C:8]1=[CH:7][C:6](=[O:22])[CH2:5][C@H:4]2[CH3:23].[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][C@H:32]([CH3:45])[C:31]1=[CH:30][C:29](=[O:46])[CH2:28][CH2:27]2.[CH3:47]OC[C@@]12[C@@H]3[C@H]([C@H]4[C@@](CC3)(C)C(=O)CC4)CCC1=CC(=O)CC2>>[CH3:25][O:1][CH2:2][C@@:3]12[C@@H:20]3[C@H:11]([C@H:12]4[C@@:16]([CH2:18][CH2:19]3)([CH3:17])[C:15](=[O:21])[CH2:14][CH2:13]4)[CH2:10][CH2:9][C:8]1=[CH:7][C:6](=[O:22])[CH2:5][C@H:4]2[CH3:23].[CH3:47][O: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][C@H:32]([CH3:45])[C:31]1=[CH:30][C:29](=[O:46])[CH2:28][CH2:27]2

Participants

5

Reactant 3

HCID 5415304219-Methoxyandrost-4-ene-3,17-dioneHCID 5427936919-Hydroxy-1beta-methyl-4-androsten-3,17-dioneHCID 7058392519-Hydroxy-6alpha-methyl-4-androstene-3,17-dione

Product 2

HCID 7058596519-Methoxy-6alpha-methyl-4-androstene-3,17-dioneHCID 7058597719-Methoxy-1beta-methyl-4-androstene-3,17-dione

Procedure

Using essentially the same procedure but substituting 19-hydroxy-1β-methyl-4-androstene-3,17-dione and 19-hydroxy-6α-methyl-4-androstene-3,17-dione for the 19-hydroxyandrost-4-ene-3,17-dione above results in the formation of 19-methoxy-1β-methyl-4-androstene-3,17-dione and 19-methoxy-6α-methyl-4-androstene-3,17-dione.

Sources & evidence

ORD record
ord-2ec3f0d4cfcb4ef893b3d67a0d649070
Source dataset
uspto-grants-1980_12
Patent number
US04239681

Reaction notes

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