反应详情

温度

80 °C

6-(Trans-4-tert-butylcyclohexyloxy)-2-naphthaldehyde (300 mg, 0.96 mmol, 1 equiv) and 3-amino-N-(phenylsulfonyl)propanamide (1.19 mmol, 1.5 equiv) were dissolved in anhydrous ethanol. The mixture was stirred at 80° C. for 1 h. Then NaBH3CN (110 mg, 1.74 mmol, 2 equiv) was added to the mixture and stirred at 80° C. for 16 h. The organic layer was concentrated and purified by preparative thin layer chromatography (mobile phase was methanol:dichloromethane 1:10) to give 3-((6-(trans-4-tert-butylcyclohexyloxy)naphthalen-2-yl)methylamino)-N-(phenylsulfonyl)propanamideas a white solid. 284 mg, white solid, 62%. ESI-MS: 523.0 (M+H)+. HPLC: 99.42%. 1H NMR (400 MHz, DMSO-d6) δ: 7.91 (s, 1H), 7.85˜7.82 (m, 2H), 7.74˜7.72 (m, 2H), 7.53˜7.51 (m, 1H), 7.41˜7.35 (m, 4H), 7.20˜7.15 (m, 1H), 4.45˜4.40 (m, 1H), 4.23 (s, 2H), 2.99 (t, 2H), 2.33 (t, 2H), 2.28˜2.16 (m, 2H), 1.89˜1.78 (m, 2H), 1.41˜1.31 (m, 2H), 1.27˜1.17 (m, 2H), 1.13˜1.06 (m, 1H), 0.89 (s, 9H).

1. stirringstirred at 80° C. for 16 h
2. concentrationThe organic layer was concentrated
3. custompurified by preparative thin layer chromatography (mobile phase was methanol:dichloromethane 1:10)
4. customto give 3-((6-(trans-4-tert-butylcyclohexyloxy)naphthalen-2-yl)methylamino)-N-(phenylsulfonyl)propanamideas a white solid