4,7alpha-Dimethyl-4-androstene-3beta,17beta,19-triol → 17beta,19-Dihydroxy-4,7alpha-dimethyl-4-androsten-3-one

HRID 1733115Notes

Reaction equation

HRID 1733115 reaction equation
[CH3:1][C:2]1[C@@H:19]([OH:20])[CH2:18][CH2:17][C@@:16]2([CH2:21][OH:22])[C:3]=1[CH2:4][C@@H:5]([CH3:24])[C@@H:6]1[C@@H:15]2[CH2:14][CH2:13][C@@:11]2([CH3:12])[C@H:7]1[CH2:8][CH2:9][C@@H:10]2[OH:23].[CH3:25][C@@H:26]1[CH2:43][C:42]2[C@:37]([CH2:45][OH:46])([CH2:38][CH2:39][C@H:40]([OH:44])[CH:41]=2)[C@@H:36]2[C@@H:27]1[C@H:28]1[C@@:32]([CH2:34][CH2:35]2)([CH3:33])[C@@H:31]([OH:47])[CH2:30][CH2:29]1>>[OH:23][C@H:10]1[CH2:9][CH2:8][C@H:7]2[C@H:6]3[C@H:15]([CH2:14][CH2:13][C@:11]12[CH3:12])[C@:16]1([CH2:21][OH:22])[C:3](=[C:2]([CH3:1])[C:19](=[O:20])[CH2:18][CH2:17]1)[CH2:4][C@H:5]3[CH3:24].[OH:47][C@@:31]1([C:1]#[C:2][CH3:3])[CH2:30][CH2:29][C@H:28]2[C@H:27]3[C@H:36]([CH2:35][CH2:34][C@:32]12[CH3:33])[C@:37]1([CH2:45][OH:46])[C:42](=[CH:41][C:40](=[O:44])[CH2:39][CH2:38]1)[CH2:43][C@H:26]3[CH3:25]

Participants

4

Reactant 2

HCID 705834934,7alpha-Dimethyl-4-androstene-3beta,17beta,19-triolHCID 705849827alpha-Methyl-4-androstene-3beta,17beta,19-triol

Product 2

HCID 5385130017beta,19-Dihydroxy-4,7alpha-dimethyl-4-androsten-3-oneHCID 13171109717beta,19-Dihydroxy-7alpha-methyl-17alpha-propinyl-4-androsten-3-one

Procedure

Substituting 4,7α-dimethyl-4-androstene-3β,17β,19-triol, 7α,17α-dimethyl-4-androstene-3β,17β,19-triol and 7α-methyl-17α-propinyl-4-androstene-3β,17β,19-triol for the 7α-methyl-4-androstene-3β,17β,19-triol above results in the formation of 17β,19-dihydroxy-4,7α-dimethyl-4-androsten-3-one, 17β,19-dihydroxy-7α,17α-dimethyl-4-androsten-3-one, 17β,19-dihydroxy-7α,17α-dimethyl-4-androsten-3-one and 17β,19-dihydroxy-7α-methyl-17α-propinyl-4-androsten-3-one, respectively.

Sources & evidence

ORD record
ord-534c2bdf594a44efa702559e8c7eb84f
Source dataset
uspto-grants-1980_12
Patent number
US04239681

Reaction notes

Loading…