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Report | Regular issue | Vol 23, No. 9, 1985, pp.2351-2356
Published online, 1st January, 1970
DOI: 10.3987/R-1985-09-2351
The Synthesis of 2’S,3R- and 2’S,3S-Hexahydronicotine

Makoto Shibagaki,* Hajime Matsushita, and Hajime Kaneko

*Life Science Research Laboratory, Japan Tobacco Inc., 6-2, Umegaoka, Midori-ku, Yokohama, Kanagawa 227-8512, Japan


The reduction of 1-benzylnicotinium bromide(4) with NaBH4 led to 1-benzyl-1,2,5,6-tetrahydronicotine(5), and the catalytic reduction of 5 over Raney nickel gave 2’S,3R- and 2’S,3S-1-benzylhexahydronicotine(6a,6b) in the ratio of 4 : 1 at room temperature. The debenzylations of 6a and 6b were carried out by the catalytic reduction over palladium on charcoal to give 2’S,3R- and 2’S,3S-hexahydronicotine(2a,2b), respectively. The configurations of 2a and 2b were determined by NMR spectra.