Reaction SMILES: Cl.Cl.[CH2:3]([O:5][C:6]([C@H:8]1[CH2:13][CH2:12][C@H:11]([NH2:14])[CH2:10][CH2:9]1)=[O:7])[CH3:4].[C:15](=O)([O-])[O-].[K+].[K+]>O>[CH2:3]([O:5][C:6]([C@H:8]1[CH2:13][CH2:12][C@H:11]([NH2:14])[CH2:10][CH2:9]1)=[O:7])[CH:4]=[CH2:15]
Reactant: CCOC(=O)[C@H]1CC[C@H](N)CC1
Reactant: O=C([O-])[O-]
Agent: Cl
Agent: [K+]
Solvent: O
Product: C=CCOC(=O)[C@H]1CC[C@H](N)CC1

Procedure:
In water was dissolved 5.0 g of trans-4-ethoxycarbonylcyclohexylamine.dihydrochloride, and after the solution was made basic by adding potassium carbonate, the solution was extracted with chloroform. The extract was washed with brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. A mixture of the residue, 5.1 g of p-toluensulfonic acid monohydrate and 50 ml of allyl alcohol was refluxed for 48 hours. The reaction mixture was concentrated, and then, diluted with chloroform. The chloroform solution was washed with an aqueous potassium carbonate solution, water and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel flash column chromatography (solvent: chloroform-methanol-aqueous ammonia (500:10:1)) to obtain 3.29 g of trans-4-(2-propenyloxycarbonyl)cyclohexylamine. (2) A mixture of 507 mg of the compound obtained in the above (1), 400 mg of (S)-1-bromoacetyl-2-cyanopyrrolidine, 714 mg of N,N-diisopropylethylamine and 4 ml of acetonitrile was stirred at 50° C. for 12 hours. After cooling to room temperature, 476 mg of N,N-diisopropylethylamine, followed by 4 ml of acetonitrile solution containing 803 mg of di-tert-butyldicarbonate were added to the reaction mixture, and the mixture was stirred at room temperature for 3 hours. After the reaction mixture was concentrated, the concentrate was diluted with ethyl acetate. The ethyl acetate solution was washed with an aqueous 10% citric acid solution, water and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (solvent: chloroform-methanol (100:1)) to obtain 658 mg of (S)-2-cyano-1-[N-tert-butoxycarbonyl-trans-4-(2-propenyloxycarbonyl)cyclohexylamino]acetylpyrrolidine. (3) A mixture of 600 mg of the compound obtained in the above (2), 165 mg of tetrakis(triphenylphosphine)palladium, 271 mg of ammonium formate and 6 ml of dioxane was stirred at 50° C. for 1 hour. After cooling, the reaction mixture was poured into water and extracted with chloroform. The extract was washed with brine, dried over anhydrous sodium sulfate, and then, the solvent was removed under reduced pressure. The residue was purified by silica gel flash chromatography (solvent: chloroform-methanol (50:1)) to obtain 394 mg of (S)-2-cyano-1-(N-tert-butoxycarbonyl-trans-4-carboxycyclohexylamino)acetylpyrrolidine. (4) A solution of 2 ml N,N-dimethylformamide containing 150 mg of the compound obtained in the above (3), 64 mg of 2-aminomethylpyridine, 114 mg of 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide and 80 mg of 1-hydroxybenzotriazole was stirred at room temperature for 24 hours. An aqueous saturated sodium hydrogencarbonate solution was added to the reaction mixture and the mixture was extracted with chloroform. The extract was washed with brine and dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The residue was dissolved in 3 ml of acetonitrile, and 1 ml of an acetonitrile solution of 118 mg of trimethylsilyl iodide was added dropwise to the solution under ice-cooling, and the mixture was stirred at room temperature for 30 minutes. To the reaction mixture were added methanol and water, and after stirring for a while, the mixture was neutralized with an aqueous saturated sodium hydrogencarbonate solution, and then, extracted with chloroform. The extract was washed with an aqueous saturated sodium hydrogencarbonate solution, water and brine, dried over anhydrous sodium sulfate, and then, the solvent was removed under reduced pressure. The residue was purified by diol chromatography (solvent:chloroform) to obtain an oily product. The oily product was dissolved in 1 ml of ethyl acetate, and then, 0.5 ml of 1N hydrochloric acid-ether followed by 2 ml of ether were added thereto, and precipitates were washed with ether to obtain 106 mg of (S)-2-cyano-1-[trans-4-(2-pyridylmethylaminocarbonyl)cyclohexylamino]acetylpyrrolidine-dihydrochloride (Example 3-1 in Table 3).