反应详情

温度

0 °C

A stirred solution of 2-adamantanamine hydrochloride (81.1 mg, 0.432 mmol) and DIEA (557 mg, 4.32 mmol) in anhydrous CH2Cl2 (5 mL) was cooled to 0° C. and CDI (84 mg, 0.52 mmol) was added. The mixture was stirred for 1 h at 0° C. and tert-butyl spiro[indoline-3,4′-piperidine]-1-carboxylate (140 mg, 0.43 mmol) in anhydrous CH2Cl2 (5 mL) was added. The reaction mixture was allowed to warm to rt and stirred overnight. The reaction mixture was concentrated and the residue was purified by preparative TLC to provide tert-butyl 1′-((2-adamantyl)carbamoyl)spiro[indoline-3,4′-piperidine]-1-carboxylate as a white solid (50 mg, 25%). 1H NMR (CD3OD, 400 MHz): δ=1.58˜2.01 (m, 28H), 2.92 (t, 2H), 3.91 (d, 2H), 4.09 (d, 2H), 5.85 (d, 1H), 6.95˜7.85 (m, 4H); MS: 466 (M++1); LC-MS (4 min) tR=2.70 min, m/z=466.

1. temperatureto warm to rt
2. stirringstirred overnight
3. concentrationThe reaction mixture was concentrated
4. customthe residue was purified by preparative TLC