反应详情

A solution of 2,8-dimethyl-1-oxa-4,8-diazaspiro[4.5]decane (1.09 g, 6.41 mmol), 3-indolepropionic acid (1.57 g, 8.3 mmol), dicyclohexylcarbodiimide (DCC, 1.78 g, 8.65 mmol) and dimethylaminopyridine (DMAP, 0.78 g, 6.41 mol) in dichloromethane (100 ml) was stirred at room temperature for 4 days. The precipitate was removed by filtration and the solvent was evaporated. Flash chromatography (silica, CH2Cl2/i-PrOH/NH4OH 85/15/1) gave the title compound that was triturated in ether. The obtained white solid (AF706), 1.1 gr (99.4% chemical purity), was filtered and dried. 1H-NMR (CDCl3, 300 MHz) δ 8.15 (br NH), 7.63 (d, J=7.76 Hz, 1H, ArH), 7.38 (d, J=7.98 Hz, 1H, ArH), 7.23 (dt, J=1.12, 7.56 Hz, 1H, ArH), 7.13 (dt, J=1.07, 7.44 Hz, 1H, ArH), 7.08 (d, J=2.15 Hz, 1H, NCHC), 4.05 (m, 1H, OCH), 3.53 (dd, J=9.0, 5.5 Hz, 1H, NCHH), 3.13 (m, 3H), 2.96 (t, J=9.2 Hz, 1H), 2.80-2.70 (m, 3H), 2.61-2.70 ((m, 2H), 2.23-2.34 (m, 2H, CH2-piperidine), 2.31 (s, 3H, NCH3), 1.37 (m, 1H, CH-piperidine), 1.33 (m, 1H, CH-piperidine), 1.25 (d, J=6.0 Hz, 3H, CH3) ppm; 13C-NMR (CDCl3, 300 MHz) δ 169.66 (C), 136.52 (C), 122.49 (CH), 121.90 (CH), 119.24 (CH), 118.78 (CH), 115.18 (C), 111.41 (CH), 94.16 (C), 69.92 (CH), 53.25 (CH2), 52.84 (CH2), 52.70 (CH2), 45.99 (CH3), 37.52 (CH2), 33.66 (CH2), 30.90 (CH2), 20.73 (CH2), 18.26 (CH3) ppm.

1. customThe precipitate was removed by filtration
2. customthe solvent was evaporated