Cl.[C:2]1([CH2:8][N:9]2[CH2:16][CH2:15][CH2:14][C@H:10]2[C:11]([OH:13])=O)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:17]1[CH:18]=CC2N(O)N=[N:23][C:21]=2[CH:22]=1.[CH3:27]N1CCOCC1.N1CCCCC1.CCN=C=NCCCN(C)C>C(Cl)Cl>[C:2]1([CH2:8][N:9]2[CH2:16][CH2:15][CH2:14][CH2:27][C@H:10]2[C:11]([N:23]2[CH2:18][CH2:17][CH2:22][CH2:21]2)=[O:13])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=11-(Phenylmethyl)-L-proline hydrochloride (2.0 g, 8.247 mmol) and HOBt (1.34 g, 9.928 mmol) were dissolved in CH2Cl2 (50 mL), and 4-methylmorpholine (2.72 mL, 24.822 mmol), piperidine (0.981 mL, 9.929 mmol), and EDCI (1.906 g, 9.928 mmol) were added to this solution. After stirring overnight, the solution was washed with water (50 mL), and the aqueous layer was extracted with CH2Cl2 (3×50 mL). The combined organic layers were dried over anhydrous MgSO4 and concentrated in vacuo to provide (2S)-1-(phenylmethyl)-2-(1-pyrrolidinylcarbonyl)piperidine (0.901 g, 40%). LCMS: (M+H)+: 273.1.
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