Reductive condensation of 3-amino-2-chloropyridine (I) with 5-isopropylbenzofuran-7-carbaldehyde (II) in the presence of sodium triacetoxyborohydride provided secondary amine (III). Displacement of the chlorine atom of (III) with phenylmagnesium bromide (IV) using NiCl2 produced phenylpyridine (V), which was hydrogenated with hydrogen over PtO2 in acetic acid to give racemic piperidine (VI). Resolution of (VI) with (R)-(-)-mandelic acid yielded the (2S,3S)-isomer, which was finally isolated as the dihydrochloride salt.