Water → 2,6-Dimethyl-3-carbomethoxy-4-(3-nitrophenyl)-5-(3-[4-(2-hydroxyethyl)phenoxy]propoxycarbonyl)-1,4-dihydropyridine

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Reaction Steps

To a solution of 2,6-dimethyl-3-carbomethoxy-4-(3-nitrophenyl)-5-(3-[4-(2-tetrahydropyran-2-yloxyethyl)phenoxy]propoxycarbonyl)-1,4-dihydropyridine (4.0 g, 6.7 mmoles) in methanol (50 mL) was added a catalytic amount of 4-toluenesulfonic acid. After 24 hours, 200 mL of CH2Cl2 and 100 mL of H2O were added. The organic extracts were dried over anhydrous Na2SO4 and the solvent evaporated. The residue (3.5 g) was purified by flash chromatography (80:20 CH2Cl2 :acetone). Evaporation of the pure fractions gave 2,6-dimethyl-3-carbomethoxy-4-(3-nitrophenyl)-5-(3-[4-(2-hydroxyethyl)phenoxy]propoxycarbonyl)-1,4-dihydropyridine (2.4 g, mp <50° C.). NMR (CDCl3)δppm: 8.1-6.5(m, 9H); 5.02(s, 1H); 4.13(t, 2H); 4.0-3.4(m, 7H); 2.68(t, 2H); 2.47(s, 1H); 2.27(s, 6 H); 2.3-1.8(m, 2H).

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