[CH3:1][N:2]([CH3:10])[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].CN(C)CCN(C)C.[CH3:19][O:20][C:21]1[N:26]=[CH:25][C:24]([CH:27]=[O:28])=[CH:23][CH:22]=1.[Cl-].[NH4+]>C1COCC1.C([Li])(CC)C>[OH:28][CH:27]([C:24]1[CH:25]=[N:26][C:21]([O:20][CH3:19])=[CH:22][CH:23]=1)[CH2:1][N:2]([CH3:10])[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6]To a solution of tert-butyl dimethylcarbamate (1.8 g, 0.012 mol) and tetramethylethylenediamine (2.6 g, 0.022 mol) in THF (anhydrous, 30 mL) was added sec-butyllithium (1.4 M in cyclohexane, 11 mL, 0.015 mmol) at −78° C. The mixture was stirred at that temperature for 30 minutes before a solution of 6-methoxy-3-pyridinecarboxaldehyde (J.Org.Chem. 55; 1; 1990; 69-73)(1.4 g, 0.01 mol, in 5 mL of dry THF) was introduced. The reaction mixture was stirred for 30 minutes, warmed to room temperature and stirred for 3 hours. Saturated ammonium chloride aqueous solution (20 mL) was added to quench the reaction after the reaction mixture was cooled to −78° C. The organic phase was separated and the aqueous phase was extracted with dichloromethane. The organic phases were combined, washed with brine and dried over sodium sulfate and concentrated. The residue was purified with a silica gel column to give the title compound (1.2 g) as a white solid.
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