4-Methyl-4,6-androstadiene-3,17,19-trione → 4,7alpha-Dimethyl-4-androstene-3beta,17beta,9-triol

HRID 1733113

Reaction equation

HRID 1733113 reaction equation
[CH3:1][C:2]1[C:19](=[O:20])[CH2:18][CH2:17][C@@:16]2(C=O)[C:3]=1[CH:4]=[CH:5][C@@H:6]1[C@@H:15]2CC[C@@]2(C)[C@H]1CCC2=O.O[C@@]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:65](CC[C@]12C)[C@:62]1([CH:63]=[O:64])[C:57](=[CH:58][C:59](=[O:68])[CH2:60][CH2:61]1)[CH:56]=[CH:55]3.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([CH3:15])[C:3]=1[CH2:4][C@@H:5]([CH3:6])[C@@H:58]1[C@:59]2([OH:68])[CH2:60][CH2:61][C@@:62]2([CH3:65])[C@H:57]1[CH2:56][CH2:55][C@@H:63]2[OH:64]

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 705854174,7alpha-Dimethyl-4-androstene-3beta,17beta,9-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,9-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-9012d0ef73d6434c9f86dd26d0ff99ad
Source dataset
uspto-grants-1980_12
Patent number
US04239681

Linked notes

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