化学合成,用于立体控制合成手性化合物。
N-叔丁氧羰基-3-哌啶酮是有机合成中间体和医药中间体,可用于实验室研发过程和化工医药合成过程中,主要用于用于立体控制合成手性化合物。
合成路线 1(1. 合成:98977-36-7)
产率:99.4%
合成条件:With sodium hypochlorite solution; sodium hydrogencarbonate; potassium bromide In dichloromethane at 5 - 10℃;
实验步骤:在步骤2中,化合物N-BOC-3-哌啶酮按照下列方案制备:向反应烧瓶中加入20.1g N-BOC-3-羟基哌啶,703.5mg PS-ABNO,100ml二氯甲烷。 向反应体系中加入1g溴化钾溶液,用冰浴冷却至5℃,将8.4g NaHCO3溶于100ml次氯酸钠溶液中,调节pH = 8.5左右,缓慢加入 控制滴加速度使反应温度不高于10,加完后,TLC检测,反应完成,PS-ABNO过滤回收,分离反应液,水相用100ml萃取 将二氯甲烷合并,合并有机相,用100ml水洗涤一次,有机相用无水Na 2 SO 4干燥,过滤,浓缩19.8g淡黄色油状产物,得到目标产物N-BOC-3-哌啶酮, 产量99.4%
参考文献:
- [1] Patent: CN107573278, 2018, A. Location in patent: Paragraph 0055; 0059-0061; 0076-0077 [2] Patent: US2011/105520, 2011, A1. Location in patent: Page/Page column 36 [3] Patent: WO2009/82134, 2009, A2. Location in patent: Page/Page column 37 [4] Patent: WO2013/13308, 2013, A1. Location in patent: Paragraph 00250-00252 [5] Patent: US2003/220341, 2003, A1. Location in patent: Page/Page column 15-16 [6] Patent: WO2006/85212, 2006, A2. Location in patent: Page/Page column 44 [7] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 6, p. 811 - 814 [8] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 20, p. 2691 - 2696 [9] Bioorganic and medicinal chemistry letters, 2002, vol. 12, # 13, p. 1785 - 1789 [10] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 13, p. 2155 - 2158 [11] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 7, p. 1645 - 1649 [12] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 9, p. 2115 - 2137 [13] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 2, p. 1022 - 1033 [14] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 1, p. 350 - 364 [15] Chemical and pharmaceutical bulletin, 2003, vol. 51, # 4, p. 390 - 398 [16] Patent: EP1375496, 2004, A1. Location in patent: Page 42-43 [17] Tetrahedron Letters, 2011, vol. 52, # 5, p. 588 - 591 [18] Journal of Organic Chemistry, 2013, vol. 78, # 23, p. 11656 - 11669 [19] Patent: CN105949113, 2016, A. Location in patent: Paragraph 0021; 0025 [20] Patent: EP1550660, 2005, A1. Location in patent: Page/Page column 10