1-(5-Cyano-2-pyridinyl)-4-piperidinecarboxylic acid → 4-{(3S,4S)-3-(4-Chloro-phenyl)-4-[(SR)-1-(5-cyano-pyridin-2-ylamino)-ethyl]-piperidine-1-carbonyl}-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-5'-carbonitrile

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In analogy to the procedure described for the synthesis of [(3RS, 4RS)-3-(4-chloro-phenyl)-4-(5-chloro-pyridin-2-yloxymethyl)-piperidin-1-yl]-[4-(3-methyl-[1,2,4]oxadiazol-5-yl)-phenyl]-methanone (example 1, step i) the title compounds were prepared from 6-{1-[(3S,4S)-3-(4-Chloro-phenyl)-piperidin-4-yl]-ethylamino}-nicotinonitrile and 5′-Cyano-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-carboxylic acid (commercially available) with subsequent separation via preparative HPLC on chiral pak AD eluting with heptane/ethanol to yield 4-{(3S,4S)-3-(4-Chloro-phenyl)-4-[(SR)-1-(5-cyano-pyridin-2-ylamino)-ethyl]-piperidine-1-carbonyl}-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-5′-carbonitrile as off-white solid. MS (m/e): 554.4 [(M+H)+] and 4-{(3S,45)-3-(4-Chloro-phenyl)-4-[(RS)-1-(5-cyano-pyridin-2-ylamino)-ethyl]-piperidine-1-carbonyl}-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-5′-carbonitrile as off-white solid. MS (m/e): 554.4 [(M+H)+]

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