Cl.[NH2:2][C@H:3]1[CH2:7][CH2:6][C@@H:5]([C:8]([O:10][CH3:11])=[O:9])[CH2:4]1.[Cl:12][C:13]1[CH:25]=[CH:24][C:16]([N:17]([CH2:21][CH2:22]Cl)[CH2:18][CH2:19]Cl)=[CH:15][CH:14]=1.C(=O)([O-])O.[Na+].[I-].[K+]>C(O)CCC>[Cl:12][C:13]1[CH:25]=[CH:24][C:16]([N:17]2[CH2:21][CH2:22][N:2]([C@H:3]3[CH2:7][CH2:6][C@@H:5]([C:8]([O:10][CH3:11])=[O:9])[CH2:4]3)[CH2:19][CH2:18]2)=[CH:15][CH:14]=1(1R,3S)-methyl 3-aminocyclopentanecarboxylate hydrochloride (1.5 g, 8.35 mmol), 4-chloro-N,N-bis(2-chloroethyl)aniline (2.32 g, 9.18 mmol), sodium hydrogencarbonate (4.91 g, 58.4 mmol), and potassium iodide (0.14 g, 0.83 mmol) were suspended in n-butanol (50 mL). The reaction mixture was stirred at 110° C. for overnight. Upon completion, the reaction mixture was evaporated under vacuo. The resulting crude residue was purified by column chromatography using ethyl acetate in hexane as eluent to obtain (1R,3S)-methyl 3-(4-(4-chlorophenyl)piperazin-1-yl)cyclopentanecarboxylate (1.5 g, 55.6%).
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