反应详情

In analogy to the procedure described for the synthesis of example 44 (step c), the title compound rac-[(3R,4S)-1-(5′-cyano-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-carbonyl)-4-(4-fluoro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-fluoro-phenyl ester was prepared from rac-[(3R,4S)-4-(4-fluoro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-fluoro-phenyl ester using 5′-cyano-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-carboxylic acid instead of 1-methylcyclopropane-1-carboxylic acid and was obtained as a brown semisolid. MS m/e: 562.1 [M]+. The racemate was then subjected to column chromatography on chiral phase to yield -[(3S,4R)-1-(5′-cyano-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-carbonyl)-4-(4-fluoro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-fluoro-phenyl ester (MS (m/e): 546.3 [M+H]+) as a yellow waxy solid and -[(3R,4S)-1-(5′-cyano-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-carbonyl)-4-(4-fluoro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-fluoro-phenyl ester (MS (m/e): 546.3 [M+H]+) as a yellow waxy solid.

1. customIn analogy to the procedure described for the synthesis of example 44 (step c)
2. customwas obtained as a brown semisolid