Reaction SMILES: [C:1]([N:6]1[C@H:11]([C:12]2[CH:17]=[C:16]([F:18])[C:15]([F:19])=[C:14]([F:20])[CH:13]=2)[CH2:10][CH2:9][CH2:8][C@@H:7]1/[CH:21]=[CH:22]/C(OC)=O)(=[O:5])[CH2:2]C=C.C(N1[C@H](C2C=C(F)C(F)=C(F)C=2)CCC[C@@H]1/C=C\C(OC)=O)(=O)CC=C.C(N(CC)CC)C>Cl[Ru](=C1N(C2C(C)=CC(C)=CC=2C)CCN1C1C(C)=CC(C)=CC=1C)(Cl)(=CC1C=CC=CC=1)[P](C1CCCCC1)(C1CCCCC1)C1CCCCC1.C(Cl)Cl>[F:18][C:16]1[CH:17]=[C:12]([C@@H:11]2[CH2:10][CH2:9][CH2:8][C@H:7]3[N:6]2[C:1](=[O:5])[CH2:2][CH:22]=[CH:21]3)[CH:13]=[C:14]([F:20])[C:15]=1[F:19]
Reactant: C=CCC(=O)N1[C@@H](/C=C/C(=O)OC)CCC[C@H]1c1cc(F)c(F)c(F)c1
Agent: Cc1cc(C)c(N2CCN(c3c(C)cc(C)cc3C)C2=[Ru](Cl)(Cl)(=Cc2ccccc2)[P](C2CCCCC2)(C2CCCCC2)C2CCCCC2)c(C)c1
Agent: C=CCC(=O)N1[C@@H](/C=C\C(=O)OC)CCC[C@H]1c1cc(F)c(F)c(F)c1
Solvent: ClCCl
Solvent: CCN(CC)CC
Product: O=C1CC=C[C@H]2CCC[C@@H](c3cc(F)c(F)c(F)c3)N12
Temperature: 25 °C
Reaction time: 0.17 h

Procedure:
Diethyl cyanophosphonate (10.0 mL) was added to a solution of methyl (2R,6S)-6-(3,4,5-difluorophenyl)piperidine-2-carboxylate (5.47 g), vinylacetic acid (5.67 mL), and triethylamine (16.8 mL) in DMF (140 mL) at 0° C., and the reaction solution was stirred at 0° C. for five hours. Ethyl acetate and saturated sodium bicarbonate water were added to the reaction solution, and the organic layer was separated. The resulting organic layer was washed with brine, dried over magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system) to obtain methyl (2R,6S)-1-(3-butenoyl)-6-(3,4,5-trifluorophenyl)piperidine-2-carboxylate. Methyl (2R,6S)-1-(3-butenoyl)-6-(3,4,5-trifluorophenyl)piperidine-2-carboxylate was dissolved in THF (120 mL). Lithium borohydride (826 mg) was added to the reaction solution at 0° C., and the reaction solution was stirred at room temperature for three hours. The reaction solution was added to a mixed solution of a cooled ammonium chloride solution in ethyl acetate, and the mixture was stirred at room temperature for 20 minutes. The organic layer was separated, dried over magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system) to obtain 1-[(2S,6R)-2-(3,4,5-trifluorophenyl)-6-(hydroxymethyl)piperidin-1-yl]-(3-buten)-1-one. DMSO (1.18 mL) was added to a solution of oxalyl chloride (1.36 mL) in dichloromethane (90 mL) in a nitrogen atmosphere at −78° C. over five minutes, and the reaction solution was stirred at −78° C. for 10 minutes. A solution of 1-[(2S,6R)-2-(3,4,5-trifluorophenyl)-6-(hydroxymethyl)piperidin-1-yl]-(3-buten)-1-one in dichloromethane (10 mL) was added to the reaction solution at −78° C. over 20 minutes, and the reaction solution was stirred at −78° C. for 20 minutes. Triethylamine (8.65 mL) was added to the reaction solution at −78° C. over 10 minutes, and then the reaction solution was stirred at −50° C. for one hour. Water and ethyl acetate were added to the reaction solution, and the organic layer was separated. The resulting organic layer was washed with brine, dried over magnesium sulfate, and then concentrated under reduced pressure to obtain a residue. Trimethyl phosphonoacetate (3.44 mL) was added to a mixed solution of 60% sodium hydride (520 mg) in THF (70 mL)-DMF (14 mL) at 0° C., and the reaction solution was stirred at room temperature for 30 minutes. A solution of the residue obtained above in THF (10 mL) was added to the reaction solution at 0° C., and the mixture was stirred at room temperature for 30 minutes. The reaction solution was added to a cooled ammonium chloride solution, followed by extraction with ethyl acetate. The resulting extract was dried over magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system) to obtain methyl (E)-3-[(2R,6S)-1-(3-butenoyl)-6-(3,4,5-trifluorophenyl)piperidin-2-yl]acrylate and methyl (Z)-3-[(2R,6S)-1-(3-butenoyl)-6-(3,4,5-trifluorophenyl)piperidin-2-yl]acrylate. A solution of a mixture of methyl (E)-3-[(2R,6S)-1-(3-butenoyl)-6-(3,4,5-trifluorophenyl)piperidin-2-yl]acrylate with methyl (Z)-3-[(2R,6S)-1-(3-butenoyl)-6-(3,4,5-trifluorophenyl)piperidin-2-yl]acrylate and Grubbs catalyst 2nd generation (707 mg) in methylene chloride (300 mL) was heated under reflux in a nitrogen atmosphere for three hours. The reaction solution was left to cool to room temperature. Then, triethylamine (1.15 mL) was added to the reaction solution, and the mixture was stirred at room temperature for 10 minutes and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system) to obtain 2.01 g of the title compound. The property value of the compound is as follows.