反应详情

A mixture of 3-amino-3-(3'-cyclopentyloxy-4'methoxyphenyl)-1-propanol (4.31 grams, 16.24 mmol) and phthalic anhydride (2.41 grams, 16.27 mmol) was melted with a heat gun for 6 minutes. The mixture was allowed to cool to room temperature. Chromatography (silica gel 100 grams, 1:5 EtOAc:CH2Cl2) gave 3-(3'-cyclopentyloxy-4'-methoxyphenyl)-3-phthalimido-1-propanol as solid, (4.97 grams, 77% yield): mp, 59.0°-61.0° C.; 1H NMR (CDCl3)δ1.56-1.98 (m, 9H, OH, C5H8), 2.48-2.59 (m, 1H, CHH), 2.71-2.83 (m, 1H, CHH), 3.66-3.74 (m, 2H, OCH2), 3.80 (s, 3H, CH3), 4.74-4.80 (m, 1H, CH), 5.51 (dd, J=6.5, 9.4 Hz, 1H, NCH), 6.78 (J=8.3 Hz, 1H, Ar), 7.05-7.09 (m, 1H, Ar), 7.16-7.17 (m, 1H, Ar), 7.64-7.70 (m, 2H, Ar), 7.75-7.81 (m, 2H, Ar); 13C NMR (CDCl3)δ24.02, 32.71, 38.84, 51.44, 55.94, 59.75, 80.35, 111.58, 115.06, 120.54, 123.12, 131.60, 131.80, 133.86, 147.48, 149.55, 168.43; Anal Calcd for C23H25NO5 : C, 69.86; H, 6.37; N, 3.54. Found: C, 69.51; H, 6.41; N, 3.54.