Bis(trimethylsilyl) peroxide → 1,1-dimethylethyl hexahydro-3-hydroxy-7-[(4-morpholinyl)methyl]-2-oxo-1H-azepine-1-carboxylate
Reaction equation
Cl.Cl.N=[C:4]1[CH:10]([OH:11])[CH2:9][CH2:8][CH2:7][CH:6]([CH2:12][N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[NH:5]1.C(C1CCCCC(=O)N1[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=C.C[Si]([O:40]O[Si](C)(C)C)(C)C>>[OH:11][CH:10]1[CH2:9][CH2:8][CH2:7][CH:6]([CH2:12][N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[N:5]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C:4]1=[O:40]Participants
4
Procedure
hexahydro-2-imino-7-[(4-morpholinyl)methyl]-1H-azepin-3-ol, dihydrochloride ##STR220## 215 A) The product of Example 214, part A, 1,1-dimethylethyl 2-ethenylhexahydro-7-oxo-1H-azepine-1-carboxylate, is treated with an organo lithium base at low temperature to generate the enolate which is subsequently reacted with bis(trimethylsilyl)peroxide by the methods of F. A. Davis et al Tettrahodron Lett. 1988, 29, 4269 and L. Camici et al Tettrahodron Lett. 1988, 29, 4197 to yield 1,1-dimethylethyl hexahydro-3-hydroxy-7-[(4-morpholinyl)methyl]-2-oxo-1H-azepine-1-carboxylate.
Sources & evidence
- ORD record
- ord-1e961fe72ccf45e4b57298239c618ac4
- Source dataset
- uspto-grants-1999_03
- Patent number
- US05883251
Reaction notes
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