[N-:1]=[N+:2]=[N-:3].[Na+].[Cl:5][C:6]1[C:11]([O:12][CH2:13][C@@H:14]2[CH2:16][O:15]2)=[CH:10][CH:9]=[CH:8][N:7]=1.O.[N-]=[N+]=[N-].[Na+]>O.O1CCOCC1>[N:1]([CH2:16][C@H:14]([OH:15])[CH2:13][O:12][C:11]1[C:6]([Cl:5])=[N:7][CH:8]=[CH:9][CH:10]=1)=[N+:2]=[N-:3]Dissolve sodium azide (22.84 g, 351.3 mmol) in water (195 mL). Separately, dissolve 2-chloro-3-[[(2S)-oxiran-2-yl]methoxy]pyridine (32.6 g, 175.6 mmol) in 1,4-dioxane (800 mL). Slowly add the water/sodium azide solution to the dioxane solution; heat to 90° C.; and stir for 1 hour. Cool the mixture and concentrate it under reduced pressure. Add water; extract with EtOAc (2×); combine the extracts; dry the combined extracts over Na2SO4; filter; and collect the filtrate. Remove the solvents under reduced pressure to provide the title compound (40.28 g, 92.8%) as a reddish white solid. MS (m/z): 229 (M+1).
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