反应详情

温度

23 °C

To a stirred mixture of 5-{2-[2-(3-chloro-phenyl)-2-hydroxy-ethylamino]-propyl}-benzo[1,3]dioxole-2,2-dicarboxylic acid (1.0 g, 2.37 mmol), and 2-methoxy-1-ethanol (10 mL) was added excess HCl(g). The mixture became homogeneous and was stirred at 23° C. After 12 h, the solution was concentrated, and chromatographed on silica gel, eluting with CHCl3 /MeOH (1/0, then 40/1, 20/1 and 10/1) to give fractions containing 5-{2-[2-(3-chloro-phenyl)-2-hydroxy-ethylamino]-propyl}-benzo[1,3]dioxole-2,2-dicarboxylic acid bis-(2-methoxy-ethyl) ester (Rf =0.37 (10/1 CHCl3 /MeOH)) as a viscous oil. This oil was dissolved in Et2O (10 mL) and HCl(g) was bubbled through the solution for 1 min. The resulting solution was evaporated to give 1.06 g (78%) of 5-{2-[2-(3-chloro-phenyl)-2-hydroxy-ethylamino]-propyl}-benzo[1,3]dioxole-2,2-dicarboxylic acid bis-(2-methoxy-ethyl) ester hydrochloride salt as a white solid; 1H NMR (300 MHz, CDCl3): δ 1.33 (brm, 3H), 2.75-2.88 (brm, 1H), 3.10-3.30 (brm, 2H), 3.35 (s, 6H), 3.40-3.53 (brm 2H), 3.63-3.68 (complexm, 4H), 4.40-4.48 (brm, 4H), 5.40-5.50 (brd, 1H), 5.50-5.75 (brs, 1H), 6.70-6.91 (complex m, 4H), 7.18-7.38 (m, 2H), 7.43 (s, 1H), 8.60-8.85 (brs, 1H), 9.90-10.15 (brs, 1H); MS (ES) m/z (relative intensity): 538 (M+ -HCl, 100).

1. concentrationthe solution was concentrated
2. customchromatographed on silica gel
3. washeluting with CHCl3 /MeOH (1/0
4. custom40/1, 20/1 and 10/1) to give fractions
5. customHCl(g) was bubbled through the solution for 1 min
6. customThe resulting solution was evaporated