C(OC(=O)[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([CH:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)[CH2:10][CH2:9]1)(C)(C)C.[ClH:20].O1CCCC1>CO.C(O)(C)C>[Cl-:20].[CH:14]1([N:11]2[CH2:10][CH2:9][CH:8]([NH3+:7])[CH2:13][CH2:12]2)[CH2:18][CH2:17][CH2:16][CH2:15]1(1-Cyclopentyl-piperidin-4-yl)-carbamic acid tert-butyl ester (3) (6.70 g, 25 mmol, 1 equiv) was dissolved in methanol (30 mL), followed by the addition of 6 N HCl in isopropanol (10 mL). The solution was stirred at room temperature for 24 hours. Due to the incompleteness of the reaction, 6 N HCl in isopropanol (10 mL) and methanol (50 mL) were added to the solution. The solution was stirred at room temperature for another 24 hours. LC-MS indicated incompletion of the reaction. Tetrahydrofurane (20 mL), 6 N HCl in isopropanol (10 mL) and methanol (200 mL) were added to the solution. The solution was stirred at room temperature for 5 hours, followed by the addition of 6 N HCl in isopropanol (10 mL). The solution was stirred at room temperature for 72 hours. The solution was evaporated under reduced pressure to obtain 4 (4.20 g, 25 mmol, quantitative). LRMS (ES+): m/z 169.
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