17beta,19-Dihydroxy-1alpha-methyl-4-androsten-3-one dipropionate → 19-Hydroxy1alpha-methyl-4-androstene-3,17-dione
Reaction equation
[C:1]([OH:5])(=O)[CH2:2][CH3:3].[OH:6][CH2:7][C@@:8]12[C@@H:25]3[C@H:16]([C@H:17]4[C@@](C[CH2:24]3)(C)C(=O)[CH2:19][CH2:18]4)[CH2:15][CH2:14][C:13]1=[CH:12][C:11](=[O:27])[CH2:10][C@@H:9]2[CH3:28].[C:29](O)(=O)CC.C(O)(=O)CC.[OH:39][C@H:40]1[CH2:45][CH2:44][C@H:43]2[C@H]3[C@H]([CH2:58][CH2:59][C@:41]12C)[C@]1(CO)C(=CC(=O)C[C@@H]1C)C[C@H]3C.C(O)(=O)CC.C(O)(=O)CC.O[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@]12C)[C@]1(CO)C(=CC(=O)C[C@@H]1C)CC3>>[OH:6][CH2:7][C@@:8]12[C@@H:25]3[C@H:16]([C@H:17]4[C@@:2]([CH2:3][CH2:24]3)([CH3:29])[C:1](=[O:5])[CH2:19][CH2:18]4)[CH2:15][CH2:14][C:13]1=[CH:12][C:11](=[O:27])[CH2:10][C@@H:9]2[CH3:28].[OH:6][C@H:7]1[CH2:11][CH2:12][C@H:13]2[C@H:14]3[C@H:3]([CH2:28][CH2:9][C@:8]12[CH3:25])[C@:2]1([CH2:1][OH:5])[C:59](=[CH:41][C:40](=[O:39])[CH2:45][C@@H:44]1[CH3:43])[CH2:58][C@H:15]3[CH3:16]Participants
5
Reactant 3
Product 2
Procedure
Substituting 17β,19-dihydroxy-1α,17α-dimethyl-4-androsten-3-one dipropionate, 19-hydroxy-1α-methyl-4-androstene-3,17-dione propionate, 17β,19-dihydroxy-1α,7α-dimethyl-4-androsten-3-one dipropionate and 17β,19-dihydroxy-1α,6α,17α-trimethyl-4-androsten-3-one dipropionate for the 17β,19-dihydroxy-1α-methyl-4-androsten-3-one dipropionate above results in the formation of 17β,19-dihydroxy-1α,17α-dimethyl-4-androsten-3-one, 19-hydroxy-1α-methyl-4-androstene-3,17-dione, 17β,19-dihydroxy-1α,7α-dimethyl-4-androsten-3-one and 17β,19-dihydroxy-1α,6α,17α-trimethyl-4-androsten-3-one, respectively.
Sources & evidence
- ORD record
- ord-18e720fd4b0c40c6bdaabddfdf72ce87
- Source dataset
- uspto-grants-1978_01
- Patent number
- US04071624
Reaction notes
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