19-Hydroxy-1alpha-methyl-4-androsten-3,17-dione propionate → 17beta,19-Dihydroxy-1alpha,6alpha-dimethyl-4-androsten-3-one
Reaction equation
[C:1]([OH:5])(=O)[CH2:2][CH3:3].[C:6](O)(=O)CC.[OH:11][C@H:12]1[CH2:17][CH2:16][C@H:15]2[C@H:18]3[C@H:29]([CH2:30][CH2:31][C@:13]12[CH3:14])[C@:26]1([CH2:27]O)[C:21](=[CH:22][C:23](=[O:33])[CH2:24][C@@H:25]1[CH3:32])[CH2:20][C@H:19]3[CH3:34].C(O)(=O)CC.C(O)(=O)CC.O[C@H:46]1CC[C@H:49]2[C@H:52]3[C@H:63]([CH2:64]C[C@:47]12C)[C@:60]1([CH2:61][OH:62])[C:55](=[CH:56][C:57](=[O:67])[CH2:58][C@@H:59]1[CH3:66])[C@@H:54](C)[CH2:53]3.C(O)(=O)CC.OC[C@@]12[C@@H]3[C@H]([C@H]4[C@@](CC3)(C)C(=O)CC4)CCC1=CC(=O)C[C@@H]2C>>[OH:11][C@H:12]1[CH2:17][CH2:16][C@H:15]2[C@H:18]3[C@H:3]([CH2:30][CH2:31][C@:13]12[CH3:14])[C@:2]1([CH2:1][OH:5])[C:21](=[CH:22][C:23](=[O:33])[CH2:24][C@@H:25]1[CH3:32])[C@@H:26]([CH3:27])[CH2:29]3.[OH:62][CH2:61][C@@:60]12[C@@H:63]3[C@H:52]([C@H:49]4[C@@:2]([CH2:3][CH2:64]3)([CH3:6])[C:1](=[O:5])[CH2:46][CH2:47]4)[CH2:53][CH2:54][C:55]1=[CH:56][C:57](=[O:67])[CH2:58][C@@H:59]2[CH3:66].[OH:11][C@H:12]1[CH2:17][CH2:16][C@H:15]2[C@H:18]3[C@H:3]([CH2:30][CH2:31][C@:13]12[CH3:14])[C@:2]1([CH2:1][OH:5])[C:21](=[CH:22][C:23](=[O:33])[CH2:24][C@@H:25]1[CH3:26])[CH2:20][C@H:19]3[CH3:34]Participants
6
Reactant 3
Product 3
Procedure
Substituting 17β,19-dihydroxy-1α,7α-dimethyl-4-androsten-3-one dipropionate, 17β,19-dihydroxy-1α,6α-dimethyl-4-androsten-3-one dipropionate, 19-hydroxy-1α-methyl-4-androsten-3,17-dione propionate and 17β,19-dihydroxy-1α,7α-dimethyl-4-androsten-3-one dipropionate in the above procedure results in the preparation of 17β,19-dihydroxy-1α,17α-dimethyl-4-androsten-3-one, 17β,19-dihydroxy-1α,6α-dimethyl-4-androsten-3-one, 19-hydroxy-1α-methyl-4-androstene-3,17-dione and 17β,19-dihydroxy-1α,7α-dimethyl-4-androsten-3-one, respectively.
Sources & evidence
- ORD record
- ord-fffd0430283f43d781e50c9ea69775f8
- Source dataset
- uspto-grants-1979_02
- Patent number
- US04139617
Reaction notes
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