3-溴丙基氨基甲酸苄酯主要作为医药合成中间体,用于制备含哌嗪结构的药物分子(如3-(4-(3-氯苯基)哌嗪-1-基)丙-1-胺二盐酸盐)。
医药合成中间体
路线1:
- 步骤:将3-溴丙胺氢溴酸盐(5.0g,22.8mmol)溶解在NaOH水溶液(15wt%,80ml)中并在氮气下冷却至0℃,滴加氯甲酸苄酯;将反应物搅拌过夜,加入乙酸乙酯(100ml)并分离各相,用HCl溶液(2M,100ml)、NaOH溶液(2M,100ml)、盐水(100ml)洗涤有机相,用Na₂SO₄干燥,蒸发得到产物。
- 条件:Stage #1: With sodium hydroxide In water, Inert atmosphere; Stage #2: Inert atmosphere
- 收率:100%
- 参考文献:[1] Patent: WO2012/95628, 2012, A1. Location in patent: Page/Page column 20 [2] Journal of Labelled Compounds and Radiopharmaceuticals, 1996, vol. 38, #1, p. 31 - 40 [3] Journal of Organic Chemistry, 2000, vol. 65, #26, p. 8979 - 8987 [4] Journal of Medicinal Chemistry, 2006, vol. 49, #17, p. 5273 - 5281 [5] Journal of Medicinal Chemistry, 2001, vol. 44, #19, p. 3175 - 3186 [6] Patent: WO2010/38948, 2010, A2. Location in patent: Page/Page column 47 [7] Chemistry - A European Journal, 2016, vol. 22, #48, p. 17226 - 17238 [8] Journal of Medicinal Chemistry, 1981, vol. 24, #4, p. 408 - 428 [9] Patent: WO2004/98644, 2004, A1. Location in patent: Page/Page column 58 [10] Patent: US5411980, 1995, A
路线2:
- 步骤:将TEA(6.91g,68.5mmol)滴加到冰冷却的3-溴丙胺氢溴酸盐(10.0g,45.6mmol)和N-(苄氧基羰氧基)-琥珀酰亚胺(11.22g,47.9mmol)的DCM溶液(200毫升)中;将搅拌的混合物温热至室温过夜,然后用水(3x)、盐水洗涤,干燥(MgSO₄),过滤并浓缩得到产物。
- 条件:With triethylamine In dichloromethane at 0 - 20℃
- 收率:92%
- 参考文献:[1] Patent: WO2007/82331, 2007, A1. Location in patent: Page/Page column 100-101