4-(羟甲基)环己烷羧酸甲酯在医药和农药领域有应用,具体用途需结合相关研究和专利进一步明确。
医药; 农药
路线1:硼烷-二甲基硫醚络合物还原法
- 步骤: 在-78℃下,向4-(甲氧基羰基)环己烷羧酸的无水THF溶液中,在20分钟内滴加硼烷-甲基硫醚络合物,将混合物搅拌3小时,然后使其缓慢达到室温。用水淬灭反应,并用EtOAc萃取混合物,有机相用盐水洗涤,经MgSO₄干燥并真空浓缩,得到标题化合物。
- 条件: With borane-dimethyl sulfide complex In tetrahydrofuran at -78℃; for 3.33 h; 缓慢达到室温
- 产率: 95%
- 参考文献: [1] Patent: US2012/165347, 2012, A1. Location in patent: Page/Page column 43 [2] Patent: CN105566324, 2016, A. Location in patent: Paragraph 0379; 0380; 0381; 0382 [3] Patent: WO2014/28597, 2014, A2. Location in patent: Page/Page column 54 [4] Patent: US2015/191434, 2015, A1. Location in patent: Paragraph 0295 [5] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 6, p. 1564 - 1568 [6] Patent: US2014/121400, 2014, A1. Location in patent: Paragraph 0083-0086 [7] Patent: WO2017/79867, 2017, A1. Location in patent: Page/Page column 126; 127 [8] Patent: US2018/2276, 2018, A1. Location in patent: Paragraph 0127-0139 [9] Patent: US2018/22716, 2018, A1. Location in patent: Paragraph 0332 [10] Patent: US2018/312481, 2018, A1. Location in patent: Paragraph 0091-0092
路线2:浓硫酸催化酯化法
- 步骤: 向4-羟甲基环己烷羧酸的甲醇溶液中加入浓硫酸,将混合物温热至回流并搅拌2小时,冷却反应混合物并加入NH₄OH直至碱性,然后用乙酸乙酯萃取,合并的有机萃取液用饱和NaCl水溶液洗涤,经无水Na₂SO₄干燥,过滤,并在减压下浓缩,得到标题化合物。
- 条件: for 2 h; Heating / reflux
- 产率: 83%
- 参考文献: [1] Patent: WO2006/69196, 2006, A1. Location in patent: Page/Page column 66 [2] Patent: US2011/269954, 2011, A1. Location in patent: Page/Page column 25
路线3:硼烷-二甲基硫醚络合物还原法(另一种描述)
- 步骤: 在冰浴冷却下,向4-(甲氧基羰基)环己烷羧酸的THF溶液中缓慢滴加硼烷的二甲基硫醚,保持反应温度在15°C,反应混合物在15°C下搅拌3小时,随后将反应液缓慢倒入冰浴冷却的甲醇中,继续在15°C下搅拌30分钟,之后进行真空浓缩,将浓缩后的残余物用水和乙酸乙酯分配,水层用乙酸乙酯萃取,合并的有机层用饱和盐水洗涤,无水硫酸钠干燥,过滤后真空浓缩,得到标题化合物。
- 条件: for 3 h; 15°C; 缓慢倒入冰浴冷却的甲醇
- 产率: 90%
- 参考文献: [1] Patent: US2012/165347, 2012, A1. Location in patent: Page/Page column 43 [3] Patent: WO2014/28597, 2014, A2. Location in patent: Page/Page column 54 [4] Patent: US2015/191434, 2015, A1. Location in patent: Paragraph 0295 [5] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 6, p. 1564 - 1568