作为医药中间体或关键原料,用于相关药物的合成制备。
医药
合成路线 1(1. 合成:147291-66-5)
产率:98%
合成条件:With hydrogen In ethanol at 20℃; for 0.50 h;
实验步骤:步骤2:3-氨基苄基氨基甲酸叔丁酯(3)的合成; 向3-硝基苄基氨基甲酸叔丁酯(2,0.69g,2.73mmol)的乙醇(20mL)溶液中加入10%Pd-C(50mg),将得到的混合物在室温,氢气氛下搅拌30分钟。分钟。 通过TLC监测反应进程。 反应完成后,将反应混合物通过硅藻土过滤并用乙醇洗涤。 减压下从滤液中蒸发乙醇,得到3-氨基苄基氨基甲酸叔丁酯(3,0.6g,98%)。 NMR(400MHz,CDCl 3):δ7.22(s,1H),7.10-7.00(t,1H),6.70-6.60(d,1H),6.60-6.50(m,1H),4.20(bs) ,2H),1.40(s,9H)。
参考文献:
- [1] Patent: WO2011/140338, 2011, A1. Location in patent: Page/Page column 60-61 [2] Chemical Communications, 2014, vol. 50, # 97, p. 15305 - 15308 [3] Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 19, p. 4189 - 4206 [4] Journal of Medicinal Chemistry, 1998, vol. 41, # 15, p. 2858 - 2871 [5] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 6, p. 883 - 886 [6] Bioorganic and medicinal chemistry letters, 2003, vol. 13, # 2, p. 209 - 212 [7] Journal of Medicinal Chemistry, 2002, vol. 45, # 4, p. 944 - 954 [8] Patent: WO2009/131687, 2009, A2. Location in patent: Page/Page column 159 [9] Patent: US7105508, 2006, B1. Location in patent: Page/Page column 71 [10] Patent: WO2012/68251, 2012, A2. Location in patent: Page/Page column 46
合成路线 2(2. 合成:147291-66-5)
产率:100%
合成条件:at 20℃;
实验步骤:将3-(氨基甲基)苯胺(1.3g,11mmol)溶解在乙腈(3.0mL)中,在室温下缓慢滴加在乙腈中的二羧酸叔丁酯(2.2g,10mmol)的溶液(3.0mL)。 将反应溶液搅拌过夜,用乙酸乙酯稀释,并通过硅胶层过滤。 浓缩母液并真空干燥,得到标题化合物(2.3g,定量)。 1 H NMR(300MHz,CDCl 3)8ppm:1.46(s,9H),3.67(s,2H),4.22(d,J = 5.9Hz,2H),4.82(S,1H),6.56-6。 63(m,2H),6.66(d,J = 7.6HZ,1H),7.11(t,J = 7.9Hz,1H)。
参考文献:
- [1] Journal of Medicinal Chemistry, 2003, vol. 46, # 9, p. 1661 - 1669 [2] Patent: WO2004/46107, 2004, A1. Location in patent: Page 233-234 [3] Patent: US2003/149027, 2003, A1 [4] Patent: WO2011/17009, 2011, A1. Location in patent: Page/Page column 105 [5] Patent: WO2009/42694, 2009, A1. Location in patent: Page/Page column 84-85 [6] Patent: US6344465, 2002, B1. Location in patent: Page column 28 [7] Journal of Medicinal Chemistry, 1999, vol. 42, # 14, p. 2504 - 2526 [8] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 2, p. 309 - 312 [9] Patent: US2003/119751, 2003, A1 [10] Patent: US2007/238746, 2007, A1. Location in patent: Page/Page column 20 [11] European Journal of Medicinal Chemistry, 2016, vol. 122, p. 178 - 184 [12] Patent: WO2016/160617, 2016, A2. Location in patent: Paragraph 00381 [13] Patent: WO2010/93419, 2010, A1. Location in patent: Page/Page column 250