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Note | Regular issue | Vol 71, No. 5, 2007, pp.1183-1192
Published online, 9th March, 2007
DOI: 10.3987/COM-07-11025
Preparation of a 1-Unsubstituted-2,3-Dihydro-1-benzazepine Derivative

Atsuko Nishiguchi,* Tomomi Ikemoto, Tatsuya Ito, Shotaro Miura, and Kiminori Tomimatsu

*Chemical Development Laboratories, Takeda Pharmaceutical Company, Ltd., 17-85 Jusohonmachi 2-chome, Yodogawa-ku, Osaka 532-8686, Japan


We developed a three-step method of producing a 1-unsubstituted-2,3-dihydro-1-benzazepine derivative (2) from 11. The alkylation of 9, obtained from 11, and the subsequent intramolecular condensation of 12 in dialkyl carbonate with a metal alcoholate were conducted in one pot to afford 1-benzazepine (13) in good yield. 13 was then hydrolyzed to give 2 in 48% overall yield from 11. Furthermore, we synthesized the orally active CCR5 antagonist intermediate 18 from 2.