[C:1]([CH:3]1[CH2:8][CH:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:6][CH2:5][N:4]1[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])#[N:2].[N-:24]=[N+:25]=[N-:26].[Na+].Cl.C(N(CC)CC)C>C1(C)C=CC=CC=1>[NH:24]1[C:1]([CH:3]2[CH2:8][CH:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:6][CH2:5][N:4]2[C:14]([O:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[O:15])=[N:2][N:26]=[N:25]11-Benzyl 4-ethyl 2-cyanopiperidine-1,4-dicarboxylate (2.5 g, 7.90 mmol) was dissolved in toluene (50 mL) and sodium azide (0.822 g, 12.64 mmol) and triethylamine hydrochloride (1.740 g, 12.64 mmol) were added and the mixture was heated at 95° C. overnight. The reaction mixture was allowed to cool to room temperature and was washed with 2 M HCl. The aqueous phase was extracted with EtOAc and the combined organic phase was dried over Na2SO4 and evaporated to yield 1-benzyl 4-ethyl 2-(1H-tetrazol-5-yl)piperidine-1,4-dicarboxylate (2.8 g, 99%). MS m/z 360 (M+H)+
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