[NH:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[CH2:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].Cl[C:15]1[C:24]([N+:25]([O-:27])=[O:26])=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][N:16]=1.C([O-])([O-])=O.[K+].[K+].C(N(CC)CC)C>C1COCC1>[C:10]([O:9][C:7](=[O:8])[CH2:6][CH:2]1[CH2:3][CH2:4][CH2:5][N:1]1[C:15]1[C:24]([N+:25]([O-:27])=[O:26])=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][N:16]=1)([CH3:13])([CH3:12])[CH3:11]Tert-butyl 2-(pyrrolidin-2-yl)acetate (1.00 g, 5.40 mmol) was added to a solution of methyl 6-chloro-5-nitronicotinate (1.169 g, 5.40 mmol) in THF (Volume: 10 ml). The reaction mixture was stirred at rt for 1 h and K2CO3 (0.760 g, 5.50 mmol) was added. The reaction mixture was stirred for 2 h and triethylamine (0.379 ml, 2.70 mmol) was added. The mixture was stirred for 1 h, filtered and concentrated in vacuo. Flash column chromatography on silica gel (120 g SiO2, hexanes:ethyl acetate 9:1) afforded methyl 6-(2-(2-tert-butoxy-2-oxoethyl)pyrrolidin-1-yl)-5-nitronicotinate (1.79 g, 4.90 mmol, 91% yield) as a yellow oil. [M+H] calc'd for C17H23N3O6, 365; found, 365.
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