[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:19]I.[Cl-].[Na+]>CN(C)C=O>[C:1]([O:5][C:6]([N:8]([CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)[CH3:19])=[O:7])([CH3:4])([CH3:2])[CH3:3]
A solution of 2-[2-(N-t-butoxycarbonylamino)ethyl]-pyridine (1.8 g) in N,N-dimethylformamide (7 ml) was added dropwise to a suspension of sodium hydride (0.39 g) in N,N-dimethylformamide (7 ml) which was cooled at 0° C. The mixture was stirred at 0° C. for 1 hour. Methyl iodide (1.4 g) was added to this solution at the same temperature. After stirring at 0° C. for 1 hour and at ambient temperature for 2 hours, the mixture was poured into ice water, saturated with sodium chloride, and extracted with ethyl acetate 3 times. The combined organic layer was washed with saturated sodium thiosulfate, saturated sodium bicarbonate and saturated sodium chloride successively, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified with silica gel chromatography (ethyl acetate:n-hexane, 3:1, V/V, as eluent) to give 2-[2-(N-t-butoxycarbonyl-N-methylamino)ethyl]-pyridine (1.47 g) as an oil.
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