反应详情

A solution of 4-(1-isopropyl-4,4,6-trimethyl-1,2,3,4-tetrahydroquinolin-7-ylamino)-benzoic acid ethyl ester (Compound 46, 64.4 mg, 0.1692 mmol), acetaldehyde (37.2 mg, 0.8462 mmol), sodium cyanoborohydride (53.2 mg, 0.8462 mmol), acetic acid (0.125 mL), and acetonitrile (1 mL) was stirred at room temperature overnight. The solvent was removed and the residue was purified by silica gel chromatography (10% ethyl acetate in hexane, Rf=0.44) to give the title compound (71.2 mg, 52%) as a solid: 1H NMR (300 MHz, CDCl3): δ1.15 (d, 6 H, J=6.5 Hz), 1.27 (t, 3 H, J=7.1 Hz), 1.31 (s, 6 H), 1.35 (t, 3 H, J=7.1 Hz), 1.74 (t, 2 H, J=6.0 Hz), 1.96 (s, 3 H), 3.15 (t, 2 H, J=6.0 Hz), 3.68 (d, 2 H, J=5.9), 3.98 (sp, 1 H, J=6.5 Hz), 4.31 (q, 2 H, J=7.1 Hz), 6.43 (s, 1 H), 6.49 (d, 2 H, J=8.9 Hz), 7.08 (s, 1 H), 7.84 (d, 2 H, J=8.9 Hz).

1. customThe solvent was removed
2. customthe residue was purified by silica gel chromatography (10% ethyl acetate in hexane, Rf=0.44)