- 2-(2-BOC-氨基乙氧基)乙醇可用作医药合成中间体
- 危险处理
如果吸入2-(2-BOC-氨基乙氧基)乙醇，请将患者移到新鲜空气处；如果皮肤接触，应脱去污染的衣着，用肥皂水和清水彻底冲洗皮肤，如有不适感，就医；如果眼晴接触，应分开眼睑，用流动清水或生理盐水冲洗，并立即就医；如果食入，立即漱口，禁止催吐，应立即就医。
医药
合成路线 1（1. 合成：139115-91-6）
产率：100%
合成条件：at 20℃;
实验步骤：化合物100的制备：在室温下，向2-（2-氨基乙氧基）乙醇（2.10g，20mmol）的CH 2 Cl 2（40mL）溶液中加入二碳酸二叔丁酯（4.36g，20mmol）。 通过TLC监测反应。 当反应完成时，浓缩内容物并通过柱色谱法（50-70％EtOAc /己烷）纯化，得到化合物100，为无色油状物（4.21g，100％）。 分析型TLC（硅胶60），80％EtOAc的正己烷溶液，Rf = 0.30; NMR（400MHz，CDCl 3）δ5.28（br s，1H），3.74（br t，/ = 4.1Hz，2H），3.59-3.54（m，4H），3.32-3.28（m，2H），3.08（br s，1H），1.44（s，9H）; 13 C NMR（100MHz，CDCl 3）δ156.1,79.2,72.2,70.2,61.5,40.3,28.3; IR（CH 2 Cl 2）3228（br），3035,2927,2855,1523cm -1; LRMS（ESI）m / z 228.0（M + + Na）; HRMS（ESI）计算值C 9 H 20 NO 4（M + + H）m / m z 206.1392，发现206.1390。
参考文献：
- [1] Patent: WO2016/181312, 2016, A1. Location in patent: Paragraph 0386-0389 [2] Journal of Medicinal Chemistry, 2000, vol. 43, # 3, p. 475 - 487 [3] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 2, p. 727 - 729 [4] Journal of the American Chemical Society, 2013, vol. 135, # 16, p. 6184 - 6191 [5] Journal of the American Chemical Society, 2017, vol. 139, # 5, p. 2118 - 2118 [6] Patent: WO2013/170147, 2013, A1. Location in patent: Page/Page column 110; 111 [7] Angewandte Chemie - International Edition, 2015, vol. 54, # 33, p. 9659 - 9662 [8] Angew. Chem., 2015, vol. 127, p. 9795 - 9798 [9] Patent: US2016/22642, 2016, A1. Location in patent: Paragraph 0458 [10] Tetrahedron Letters, 2008, vol. 49, # 29-30, p. 4491 - 4493 [11] Patent: WO2016/118666, 2016, A1. Location in patent: Paragraph 0547; 0548; 0549 [12] Patent: US2018/72711, 2018, A1. Location in patent: Paragraph 0373; 0374 [13] Patent: US2018/99940, 2018, A1. Location in patent: Paragraph 0787-0788 [14] Patent: WO2012/168733, 2012, A1. Location in patent: Page/Page column 111-112 [15] Synthesis (Germany), 2014, vol. 46, # 10, p. 1399 - 1406 [16] Organic and Biomolecular Chemistry, 2018, vol. 16, # 32, p. 5756 - 5763 [17] Helvetica Chimica Acta, 1991, vol. 74, # 8, p. 1697 - 1706 [18] Tetrahedron Letters, 2007, vol. 48, # 39, p. 6996 - 6999 [19] Patent: EP1745802, 2007, A1. Location in patent: Page/Page column 16-17 [20] Tetrahedron Letters, 2010, vol. 51, # 49, p. 6388 - 6391 [21] Chemical Communications, 2013, vol. 49, # 43, p. 4914 - 4916 [22] Chemical Biology and Drug Design, 2013, vol. 81, # 5, p. 577 - 582 [23] Angewandte Chemie - International Edition, 2015, vol. 54, # 35, p. 10327 - 10330 [24] Angew. Chem., 2015, vol. 35, # 37, p. 10467 - 10471,5 [25] Beilstein Journal of Organic Chemistry, 2018, vol. 14, p. 2646 - 2650 [26] Tetrahedron Letters, 2008, vol. 49, # 21, p. 3527 - 3529 [27] Synthesis, 2008, # 19, p. 3126 - 3130 [28] Patent: WO2014/174060, 2014, A1. Location in patent: Page/Page column 85 [29] Patent: WO2014/174062, 2014, A1. Location in patent: Page/Page column 71 [30] Patent: WO2015/162293, 2015, A1. Location in patent: Page/Page column 182 [31] ACS Combinatorial Science, 2016, vol. 18, # 12, p. 710 - 722 [32] Chemistry - A European Journal, 2010, vol. 16, # 3, p. 878 - 889 [33] Angewandte Chemie - International Edition, 2015, vol. 54, # 5, p. 1466 - 1470 [34] Angew. Chem., 2015, vol. 127, # 5, p. 1486 - 1490,5 [35] Patent: US2015/353489, 2015, A1. Location in patent: Paragraph 0098; 0173; 0174 [36] Tetrahedron Letters, 2007, vol. 48, # 33, p. 5865 - 5868 [37] Molecules, 2013, vol. 18, # 11, p. 13957 - 13978 [38] Angewandte Chemie - International Edition, 2017, vol. 56, # 30, p. 8672 - 8676 [39] Angew. Chem., 2017, vol. 129, # 30, p. 8798 - 8802,5 [40] Patent: CN107118586, 2017, A. Location in patent: Paragraph 0534-0536 [41] European Journal of Medicinal Chemistry, 2014, vol. 82, p. 16 - 35 [42] Patent: CN104774161, 2017, B. Location in patent: Paragraph 0019; 0020; 0021 [43] Patent: WO2017/46172, 2017, A1. Location in patent: Page/Page column 83 [44] Patent: CN107670050, 2018, A. Location in patent: Paragraph 0154; 0155; 0156 [45] Patent: CN107670048, 2018, A. Location in patent: Paragraph 0155; 0157 [46] Chemistry - A European Journal, 2014, vol. 20, # 43, p. 13938 - 13944 [47] Patent: JP2016/196447, 2016, A. Location in patent: Paragraph 0041-0043 [48] Green Chemistry, 2009, vol. 11, # 3, p. 373 - 379 [49] Macromolecules, 2012, vol. 45, # 2, p. 842 - 851 [50] Journal of Molecular Structure, 2005, vol. 779, # 1-3, p. 1 - 10 [51] Patent: US2008/95699, 2008, A1. Location in patent: Page/Page column 21 [52] Patent: US2003/73862, 2003, A1 [53] Patent: WO2012/9309, 2012, A1. Location in patent: Page/Page column 41 [54] Patent: US2014/37573, 2014, A1. Location in patent: Paragraph 1120 [55] Patent: WO2015/57847, 2015, A1. Location in patent: Page/Page column 227; 228 [56] Angewandte Chemie - International Edition, 2006, vol. 45, # 30, p. 4936 - 4940 [57] Patent: US6664265, 2003, B2. Location in patent: Page column 23 [58] Patent: US2006/154854, 2006, A1. Location in patent: Page/Page column 15; sheet 2 [59] Patent: US5594023, 1997, A [60] Patent: WO2006/50941, 2006, A1. Location in patent: Page/Page column 43-44 [61] Patent: US5144043, 1992, A [62] Patent: US2006/258600, 2006, A1. Location in patent: Page/Page column 27 [63] Patent: US2003/130518, 2003, A1 [64] Patent: US2003/139441, 2003, A1 [65] Patent: US2003/187016, 2003, A1 [66] Patent: US6677347, 2004, B2 [67] Patent: WO2003/105845, 2003, A1. Location in patent: Page 102-103 [68] Patent: US6660735, 2003, B2. Location in patent: Page column 20, 21 [69] Patent: EP2123283, 2009, A1. Location in patent: Page/Page column 14 [70] Patent: US2004/87601, 2004, A1. Location in patent: Page 29 [71] Patent: EP1602362, 2005, A1. Location in patent: Page/Page column 59 [72] Patent: EP1607088, 2005, A1. Location in patent: Page/Page column 58 [73] Patent: US2009/325894, 2009, A1. Location in patent: Page/Page column 9 [74] Journal of the American Chemical Society, 2010, vol. 132, # 13, p. 4550 - 4551 [75] Patent: WO2006/50942, 2006, A1. Location in patent: Page/Page column 68 [76] Patent: WO2006/50943, 2006, A1. Location in patent: Page/Page column 49 [77] Patent: WO2011/46970, 2011, A1. Location in patent: Page/Page column 100 [78] Patent: US2011/269965, 2011, A1. Location in patent: Page/Page column 33 [79] Angewandte Chemie - International Edition, 2012, vol. 51, # 2, p. 509 - 512 [80] Biomacromolecules, 2012, vol. 13, # 10, p. 3138 - 3150,13 [81] Biomacromolecules, 2012, vol. 13, # 10, p. 3138 - 3150 [82] Patent: US2013/116263, 2013, A1. Location in patent: Paragraph 0694 [83] Chemical Communications, 2013, vol. 49, # 54, p. 6048 - 6050 [84] Patent: EP2824108, 2015, A1. Location in patent: Paragraph 0106 [85] Patent: US2015/31674, 2015, A1. Location in patent: Paragraph 0267 [86] Patent: WO2015/21092, 2015, A1. Location in patent: Page/Page column 74; 76 [87] Patent: US2015/166595, 2015, A1. Location in patent: Paragraph 0224 [88] Patent: US2015/329560, 2015, A1. Location in patent: Paragraph 0144 [89] Patent: EP2539451, 2016, B1. Location in patent: Paragraph 0123 [90] Patent: US9249179, 2016, B2. Location in patent: Page/Page column 30; 31 [91] Patent: US2016/128945, 2016, A1. Location in patent: Paragraph 0540; 0541 [92] Journal of Medicinal Chemistry, 2016, vol. 59, # 23, p. 10642 - 10660 [93] Patent: US2016/257653, 2016, A1. Location in patent: Paragraph 0375; 0376 [94] Patent: EP3321279, 2018, A1. Location in patent: Paragraph 0239 [95] Journal of the American Chemical Society, 2018, vol. 140, # 36, p. 11360 - 11369 [96] Patent: WO2005/108412, 2005, A1. Location in patent: Page/Page column 61 [97] Patent: WO2005/108413, 2005, A1. Location in patent: Page/Page column 51
合成路线 2（2. 合成：139115-91-6）
产率：78%
合成条件：Stage #1: With sodium hydrogencarbonate In dichloromethane; water at 20℃; for 0.17 h; Stage #2: at 20℃;
实验步骤：将2-（2-氨基乙氧基）乙醇（10.5g，0.1mol）和NaHCO 3（12.6g，0.15mol）加入到100mL CH 2 Cl 2和100mL H 2 O中。 将溶液在室温下搅拌10分钟，然后加入二碳酸二叔丁酯（21.8g，0.1mol）。 将得到的溶液在室温下搅拌过夜，然后用CH 2 Cl 2（3.x.100mL）萃取。 合并有机相，用无水硫酸钠干燥，真空蒸发。 将残余物进行硅胶柱色谱（CH 2 Cl 2：CH 3 OH = 50：110：1），得到2-（2-t-Boc-氨基乙氧基）乙醇（1）（16.0g，78mmol，收率78％）
参考文献：
- [1] Patent: US2005/112088, 2005, A1. Location in patent: Page/Page column 25-27 [2] Patent: WO2006/86449, 2006, A2. Location in patent: Page/Page column 98
