Efficient synthesis of (R)-6-benzyloxycarbonylamino-1-methyl-4(3-methyl-benzyl)hexahydro-1,4-diaz epine. 2. Novel formation of hexahydro-1,4-diazepine ring using 1,2,3-trisubstituted aminopropane derivative and glyoxal

摘要

An efficient and practical method for synthesis of the optically active hexahydro-1,4-diazepine 2, which is a key intermediate of DAT-582, a potent and selective serotonin-3 receptor antagonist, is described Treatment of the (R)-1,2,3-trisubstituted aminopropane dihydrochloride 5b prepared from methyl (S)-1-tritylaziridne-2-carboxylate (4) via the (S)-1-benzyloxycarbonylaziridine-2-carboximide 8 with glyoxal in the presence of NaBH3CN or boran-triethylamine complex directly gave 2 in good yield without racemization. (C) 1998 Elsevier Science Ltd. All rights reserved. [References: 9]