19-t-Butyldimethylsiloxy-4-androstene-3,17-dione → 19-t-Butyldimethylsiloxy-6-methyl-5-androstene-3,17-dione
Reaction equation
[O:1]([CH2:9][C@@:10]12[C@@H:27]3[C@H:18]([C@H:19]4[C@@:23]([CH2:25][CH2:26]3)([CH3:24])[C:22](=[O:28])[CH2:21][CH2:20]4)[CH2:17][C@H:16]([CH3:29])[C:15]1=[CH:14][C:13](=[O:30])[CH2:12][CH2:11]2)[Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3].O(C[C@@]12[C@@H]3[C@H]([C@H]4[C@@](CC3)(C)C(=O)CC4)CCC1=CC(=O)CC2)[Si](C(C)(C)C)(C)C>>[O:1]([CH2:9][C@@:10]12[C@@H:27]3[C@H:18]([C@H:19]4[C@@:23]([CH2:25][CH2:26]3)([CH3:24])[C:22](=[O:28])[CH2:21][CH2:20]4)[CH2:17][C:16]([CH3:29])=[C:15]1[CH2:14][C:13](=[O:30])[CH2:12][CH2:11]2)[Si:2]([C:5]([CH3:8])([CH3:6])[CH3:7])([CH3:4])[CH3:3]Participants
3
Procedure
Substituting 19-t-butyldimethylsiloxy-6α-methyl-4-androstene-3,17-dione, 19-(4'-tetrahydropyranyloxy)androst-4-ene-3,17-dione, 4-methyl-17β,19-di(4'-tetrahydropyranyloxy)-4-androsten-3-one and 1β-methyl-19-(4'-tetrahydropyranyloxy)-4-androsten-3,17-dione for the 19-t-butyldimethylsiloxy-4-androstene-3,17-dione above results in the preparation of 19-t-butyldimethylsiloxy-6-methyl-5-androstene-3,17-dione, 19-(4'-tetrahydropyranyloxy)androst-5-ene-3,17-dione, 4α-methyl-17β,19-di(4'-tetrahydropyranyloxy)-5-androsten-3-one and 1β-methyl-19-(4'-tetrahydropyranyloxy)-5-androsten-3,17dione, respectively.
Sources & evidence
- ORD record
- ord-d1471875fe2745f8b67da20c6ec57079
- Source dataset
- uspto-grants-1979_02
- Patent number
- US04139617
Reaction notes
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