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4-Methyl-4,6-androstadiene-3,17,19-trione → 4,7alpha-Dimethyl-4-androstene-3beta,17beta,19-triol

HRID 371853
Notes
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Reaction equation

HRID 371853 reaction equation
[CH3:1][C:2]1[C:19](=[O:20])[CH2:18][CH2:17][C@@:16]2([CH:21]=[O:22])[C:3]=1[CH:4]=[CH:5][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:10]2=[O:23].O[C@@:25]1(C)CC[C@H]2[C@H]3[C@H](CC[C@]12C)[C@]1(C=O)C(=CC(=O)CC1)C=C3.O[C@@]1(C#CC)CC[C@H]2[C@H]3[C@H](CC[C@]12C)[C@]1(C=O)C(=CC(=O)CC1)C=C3.C[C@]12CC[C@H]3[C@@H](C=CC4[C@]3(C=O)CCC(=O)C=4)[C@@H]1CCC2=O>>[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]([CH3:25])[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]
ParticipantsProcedureSources & evidenceReaction notes

Participants

5

Reactant 4

HCID 537200574-Methyl-4,6-androstadiene-3,17,19-trioneHCID 537511734,6-Androstadiene-3,17,19-trioneHCID 8673569317beta-Hydroxy-17alpha-methyl-4,6-androstadiene-3,19-dioneHCID 13171109617beta-Hydroxy-17alpha-propinyl-4,6-androstadiene-3,19-dione

Product 1

HCID 70583493
4,7alpha-Dimethyl-4-androstene-3beta,17beta,19-triol

Procedure

Substituting 4-methyl-4,6-androstadiene-3,17,19-trione, 17β-hydroxy-17α-methyl-4,6-androstadiene-3,19-dione and 17β-hydroxy-17α-propinyl-4,6-androstadiene-3,19-dione for the 4,6-androstadiene-3,17,19-trione above results in the formation of 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, respectively.

Sources & evidence

ORD record
ord-41b9081b5f8d41888de5fea46077ee34
Source dataset
uspto-grants-1978_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04087524

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes