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Paper | Regular issue | Vol 53, No. 11, 2000, pp.2471-2485
Published online, 1st January, 1970
DOI: 10.3987/COM-00-9026
A Practical Procedure for Preparation of N-(endo-8-(3-Hydroxy)propyl-8-azabicyclo[3.2.1]oct-3-yl)-1-isopropyl-2-oxo-1,2-dihydro-3-quinolinecarboxamide (TS-951)

Masaji Suzuki,* Toshie Kaneko, Hiroaki Kamiyama, Yutaka Ohuchi, and Sadakazu Yokomori

*Research Center, Taisho Pharmaceutical Co., Ltd., 1-403 Yoshino-Cho, Ohmiya, Saitama 330-8530, Japan


Effective and convergent process for the preparation of a potent and selective 5-HT4 receptor agonist, the title compound, by reaction of 1-isopropyl-2-oxo-1,2-dihydro-3-quinolinecarboxylic acid (6) with endo-3-amino-8-(3-hydroxypropyl)-8-azabicyclo[3.2.1]octane dihydrochloride (20) has been described. Furthermore, this process was developed to pilot plant scale. 1-Isopropyl-2-oxo-1,2-dihydro-3-quinolinecarboxylic acid (6) was prepared from 2-aminobenzyl alcohol (12) in 65.6% overall yield and endo-3-amino-8-(3-hydroxypropyl)-8-azabicyclo[3.2.1]octane dihydrochloride (20) was prepared from 2,5-dimethoxyfuran (16) in 43.4% overall yield.