反应详情

A 25-mL, three-necked, round-bottomed flask was equipped with a magnetic stirrer, a standard condenser with N2 inlet, a 10-mL addition funnel and two glass stoppers. To a mixture of the amine (31, 0.60 g, 3.57 mmol) in CH2Cl2 (5 mL) and 10% NaOH (3.58 g, 8.93 mmol) was added dropwise a solution of 3,4,5-trimethoxybenzoyl chloride (0.92 g, 3.92 mmol) in CH2Cl2 (5 mL) over 15 min. Stirring of the mixture was continued for an additional 3 h under N2. An aqueous mixture, upon addition of H2O (30 mL), was extracted (CH2Cl2, 4×25 mL). Combined extracts were dried (Na2SO4, 2 h), filtered, and concentrated to give a viscous yellow oil. Chromatography of the oil was performed on neutral alumina (74 g, 1.7 cm×32 cm) using 60:40 ethyl acetate/hexanes as eluant. Fractions (Rf =0.34) were saved and concentrated (rotary evaporator then vacuum pump, overnight, RT/0.2 mm Hg) to give 1.02 g (79.1%) of off-white solid (35); mp 67.5°-69.5° C. IR (KBr) cm-1 3055 (Ar C--H), 2985, 2955, 2910, 2890, 2780 (C--H), 1620 (C=O); 1H NMR (DCCl3) δ0.96 (d, 3H, CH3, J=6.5 Hz), 1.09 (d, 3H, CH3, J=6.7 Hz), 1.64-1.79 [m, 3H, H(5) and H(9)], 2.05 [bs, 1H, H(1)], 2.44 [bd, 1H, H(4)ax, J=10.6 Hz], 2.57 [bd, 1H, H(6)ax, J=10.8 Hz], 2.66 [heptet, 1H, CH(CH3)2, J=6.6 Hz], 2.71 [bd, 1H, H(6)eq, J=11.0 Hz], 3.02-3.07 [m, 2H, H(4)eq and H(2)ax ], 3.31 [bd, 1H, H(8)ax, J=13.2 Hz], 3.80-3.92 [m, 10H, H(8)eq and OCH3 ], 4.77 [bd, 1H, H(2)eq, J=13.5 Hz], 7.29 (s, 2H, Ar--H); 13C NMR (DCCl3) ppm 15.87, 19.42 (CH3), 29.02 [C(1)], 29.78 [C(5)], 32.35 [C(9)], 46.64 [C(2)], 51.73 [C(4)], 52.48 [C(8)], 54.39 [CH(CH3)2 ], 54.95 [C(6)], 56.13, 60.86 (OCH3), 103.83, 133.32, 133.21, 138.22, 153.21 (Ar--C), 169.66 (C=O). Anal. Calcd. for C20H30N 2 O4 : C, 66.27; H, 8.34. Found: C, 66.04; H, 8.32.

1. customA 25-mL, three-necked, round-bottomed flask was equipped with a magnetic stirrer, a standard condenser with N2 inlet, a 10-mL addition funnel
2. extractionwas extracted (CH2Cl2, 4×25 mL)
3. dry with materialCombined extracts were dried (Na2SO4, 2 h)
4. filtrationfiltered
5. concentrationconcentrated
6. customto give a viscous yellow oil
7. concentrationconcentrated (
8. customrotary evaporator