Cl.Cl.[C:3]1([C@@H:9]2[CH2:14][N:13]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:12][CH2:11][N:10]2CC=C)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C.[OH-].[Na+].C1(C)C=CC=CC=1>O.[Ru](Cl)(Cl)Cl>[C:3]1([C@H:9]2[NH:10][CH2:11][CH2:12][N:13]([CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:14]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1In distilled water (3 mL), (R)-2-Phenyl-4-(phenylmethyl)-1-(2-propenyl)hexahydropyrazine dihydrochloride (328 mg, 1.0 mmol) produced in Example 19 was dissolved. To the solution, ruthenium chloride (5 mg, 0.02 equivalent) and activated charcoal (6 mg) were added. The mixture was stirred at 100° C. for 24 hours. To the mixture, 30 wt % aqueous solution of sodium hydroxide (295 mg, 2.2 equivalents) and toluene (3 mL) were added. The formed insolubles were separated by filtration, and washed with toluene (3 mL). After the organic layer and aqueous layer of the filtrate were separated, the organic layer was washed twice with distilled water (6 mL). The organic layer was concentrated and dried under vacuum, to obtain 227 mg of the title compound as pale brown oil (yield: 91%, chemical purity: 94.8 area %). The retention time in the chemical purity analysis method was 2.4 min.
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