3-甲磺酰氧基吡咯烷-1-羧酸叔丁酯是一种有机合成中间体,广泛应用于医药领域的相关化合物合成。
医药
合成路线 1(1. 合成:141699-57-2)
产率:100%
合成条件:With triethylamine In dichloromethane at 0 - 20℃; for 2.50 h;
实验步骤:向搅拌的3-羟基吡咯烷-1-羧酸叔丁酯(16g,85.4mmol)和三乙胺(19mL,129mmol)在130mL CH 2 Cl 2中的溶液中加入甲磺酰氯(10mL,129mmol)在20mL CH 2 Cl 2中的溶液。 在0°C下滴加。 添加后,将反应物在室温下搅拌2.5小时,然后用饱和NaHCO 3水溶液淬灭。 NaHCO 3(水溶液),并用CH 2 Cl 2萃取。 将萃取液干燥并浓缩,得到所需产物(22.7g,100%收率),为黄色固体。
参考文献:
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合成路线 2(2. 合成:141699-57-2)
产率:63.5%
合成条件:With triethylamine In dichloromethane at 0℃; for 3.50 h;
实验步骤:叔丁基-3 - [(甲基磺酰基)氧基]吡咯烷-1-羧酸酯; 将5-羟基吡咯烷-1-羧酸叔丁酯(3.00g,16.02mmol)溶于无水DCM(50mL)中并在冰水浴中冷却。 加入甲磺酰氯(2.38g,20.83mmol),然后加入TEA(2.43g,24.03mmol),将反应混合物在0℃下搅拌3.5小时。 将反应混合物用水(250mL)洗涤,用MgSO 4干燥,过滤并蒸发。 使用Biotage Horizon HPFC系统10(40 + M柱,等度运行的庚烷/ EtOAc(50:50))纯化粗产物,得到标题化合物(2.7g,63.5%)。 1H NMR(500MHz,CDCl3):δ1.38(s,9H),2.07(bs,1H),2.18(bs,1H),2.97(s,3H),3.35-3.61(m,4H),5.16-5.18( m,IH); 13 C NMR(125MHz,CDCl 3):δ28.59,31.84,32.76,38.80,43.61,52.16,80.12,154.30。
参考文献:
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