[N:1]1([CH2:6][CH2:7][OH:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.[Na].Cl[C:11]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:12]=1[C:13]([O:15][CH3:16])=[O:14]>C1(C)C=CC=CC=1.C(Cl)Cl>[CH3:16][O:15][C:13]([C:12]1[CH:17]=[C:18]([N+:21]([O-:23])=[O:22])[CH:19]=[CH:20][C:11]=1[O:8][CH2:7][CH2:6][N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:14]3.43 g (29.8 mmol) of 2-pyrrolidin-1-ylethanol is dissolved in 60 mL of toluene and 575 mg (25.0 mmol) of sodium is added batchwise. The mixture is heated to 100° C. and then stirred for a further 12 hours at 50° C. After cooling, 5.00 g (22.5 mmol) of methyl 2-chloro-5-nitrobenzoate are added batchwise and the mixture is stirred for 1 day at ambient temperature. After this time, the solvent is eliminated, the residue is taken up in methylene chloride and washed with water. The organic phase is dried over sodium sulfate and concentrated by rotary evaporation. Finally the product is purified through a silica gel column with a gradient of methylene chloride/methanol/ammonia (8:2 to 8:2:0.1) as eluant. Yield: 1.65 g (25% of theory); Rf value: 0.45 (silica gel, methylene chloride/methanol/ammonia=9:1:0.1); C14H18N2O5; EII mass spectrum: m/z=295 [M+H]+.
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