[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH:13]([CH2:17]OS(C)(=O)=O)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:23]=[N+:24]=[N-:25].[Na+]>CN(C=O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH:13]([CH2:17][N:23]=[N+:24]=[N-:25])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Dissolved 1-benzyloxycarbonyl-3-methanesulfonyloxymethyl-piperidine (5.24 mmol, 1 eq) in DMF (50 mL). Added sodium azide (1.7 g, 26.2 mmol, 5 eq). Warmed the mixture to 60° C. and let stir overnight. Removed the DMF under reduced pressure. Diluted the residue with ethyl acetate and washed with water and then brine. Dried the organic layer over anhydrous Na2SO4, filtered and concentrated giving 1.27 g. crude product.
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