As shown in Scheme 22341901a, TER-930180 was prepared from 3-(3-pyridyl)acrolein (I) and methyl 4-(cyanomethyl)cinnamate (II). The condensation of (I) and (II) with sodium methoxide yielded a mixture of diene isomers (III), which was then hydrogenated over Pd/C in dioxane, and then over Raney Nickel at 10 approx. 15 atm of H2 in ammoniac/methanol. The amine thus obtained (IV) was treated with 4-chlorobenzenesulfonyl chloride, followed by hydrolyzation with sodium hydroxide solution, yielding TER-930180. The starting materials (I) and (II) were obtained as follows: Reduction of methyl 3-(3-pyridyl)acrylate with DIBAL, and oxidation with manganese dioxide to yield 3-(3-pyridyl)acrolein (I). Bromination of methyl 4-methylcinnamate with NBS, and cyanization with potassium cyanide in the presence of PTC produced methyl 4-cyanomethylcinnamate (II).

As shown in Scheme 22341901a, TER-930180 was prepared from 3-(3-pyridyl)acrolein (I) and methyl 4-(cyanomethyl)cinnamate (II). The condensation of (I) and (II) with sodium methoxide yielded a mixture of diene isomers (III), which was then hydrogenated over Pd/C in dioxane, and then over Raney Nickel at 10 approx. 15 atm of H2 in ammoniac/methanol. The amine thus obtained (IV) was treated with 4-chlorobenzenesulfonyl chloride, followed by hydrolyzation with sodium hydroxide solution, yielding TER-930180. The starting materials (I) and (II) were obtained as follows: Reduction of methyl 3-(3-pyridyl)acrylate with DIBAL, and oxidation with manganese dioxide to yield 3-(3-pyridyl)acrolein (I). Bromination of methyl 4-methylcinnamate with NBS, and cyanization with potassium cyanide in the presence of PTC produced methyl 4-cyanomethylcinnamate (II).