CAS: 809282-20-0; (2S,3R)-1-(Dimethylamino)-3-(3-Methoxyphenyl)-2-Methylpentan-3-Ol

该化合物是一种三级手淫酒精,其成分为二甲基氨基基基和三甲基苯基替代物,其立体化学定义结构(2R,3S)使它成为不对称合成和药物应用中有价值的中间体.甲基氧和二甲基氨基功能组的存在增强了它作为生物活性分子的构件的效用,特别是在CNS目标化合物的开发方面.该化合物的界定完善配置确保了反应的高度选择性,而其结构复杂性允许衍生为更专业的手持器.对于医学化学研究来说,它提供了对合成途径的立体化学结果的精确控制.

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CAS号175591-22-7 (2R,3R)-3-(3-甲氧... | CAS号175591-23-8 他喷他多

合成工艺路线路线简述

  • 合成目标产物 (2S,3R)-1-(Dimethylamino)-3-(3-Methoxyphenyl)-2-Methylpentan-3-Ol 主要起始原料 (S)-3-(Dimethylamino)-1-(3-Methoxyphenyl)-2-Methylpropan-1-One And Ethylmagnesium Bromide
  • 159144-11-3 + 2398-37-0 = 809282-20-0
    反应条件:1.1 Reagents: Sulfuric Acid Magnesium Salt (1:1) Solvents: Tetrahydrofuran; Rt; 1 H,Reflux; Reflux -> 5 °C1.2 Solvents: Tetrahydrofuran; 5 °C; 1 H,5 °C1.3 Reagents: Acetic Acid Solvents: Water; 5 °C; 30 Min,5 °C1.4 Reagents: Ammonia Solvents: Water; 5 °C; 10 Min,5 °C
    标题:Synthesis Of Tapentadol Hydrochloride
    作者:Cheng,Qing-Fang; Et Al
    参考文献:Zhongguo Xinyao Zazhi 日期:2013 卷标:22(14) 页码:1691-1693]

    197145-37-2 + 2743-38-6 = 809282-20-0
    反应条件:1.1 Reagents: Diethylamine Solvents: Tert-Butyl Methyl Ether; 3 H,Rt2.1 Solvents: Tetrahydrofuran; < 25 °C; 1 H,< 25 °C2.2 Reagents: Acetic Acid Solvents: Water; Cooled; 30 Min,Cooled2.3 Reagents: Ammonia Solvents: Water; 10 Min
    标题:Synthesis Of Tapentadol Hydrochloride
    作者:Ma,Hui; Et Al
    参考文献:Zhongguo Yiyao Gongye Zazhi 日期:2010 卷标:41(9) 页码:641-644]

    62708-56-9 + 197145-37-2 = 809282-20-0
    反应条件:1.1 Solvents: Ethanol; 48 H,38 °C; 38 °C -> 22 °C; 14 H,22 °C2.1 Reagents: Diethylamine Solvents: Tert-Butyl Methyl Ether; 3 H,Rt3.1 Solvents: Tetrahydrofuran; < 25 °C; 1 H,< 25 °C3.2 Reagents: Acetic Acid Solvents: Water; Cooled; 30 Min,Cooled3.3 Reagents: Ammonia Solvents: Water; 10 Min
    标题:Synthesis Of Tapentadol Hydrochloride
    作者:Ma,Hui; Et Al
    参考文献:Zhongguo Yiyao Gongye Zazhi 日期:2010 卷标:41(9) 页码:641-644]

    2386-64-3 + 850222-40-1 = 809282-20-0
    反应条件:1.1 Solvents: Tetrahydrofuran; < 25 °C; 1 H,< 25 °C1.2 Reagents: Acetic Acid Solvents: Water; Cooled; 30 Min,Cooled1.3 Reagents: Ammonia Solvents: Water; 10 Min
    标题:Synthesis Of Tapentadol Hydrochloride
    作者:Ma,Hui; Et Al
    参考文献:Zhongguo Yiyao Gongye Zazhi 日期:2010 卷标:41(9) 页码:641-644]

    2398-37-0 + 159144-13-5 = 809282-20-0
    反应条件:1.1 Reagents: Magnesium Solvents: Tetrahydrofuran; 30 °C; Reflux; 1 H,Reflux; Reflux -> 5 °C1.2 Solvents: Tetrahydrofuran; 5 °C; 17 H,30 °C; 30 °C -> -5 °C1.3 Reagents: Ammonium Chloride Solvents: Water; -5 - 0 °C; 0.5 H,-5 °C
    标题:The Objective Of This Paper Is To Study The Synthetic Technology Of (2S,3R)-1-Dimethylamino-3-(3-Methoxyphenyl)-2-Methylpentan-3-Ol
    作者:Xie,Ying; Et Al
    参考文献:Xiandai Yaowu Yu Linchuang 日期:2011 卷标:26(6) 页码:461-463]

    = 809282-20-0
    反应条件:1.1 Reagents: Sodium Hydroxide Solvents: Dichloromethane,Water; Ph 9,0 °C2.1 Reagents: Magnesium Solvents: Tetrahydrofuran; 30 °C; Reflux; 1 H,Reflux; Reflux -> 5 °C2.2 Solvents: Tetrahydrofuran; 5 °C; 17 H,30 °C; 30 °C -> -5 °C2.3 Reagents: Ammonium Chloride Solvents: Water; -5 - 0 °C; 0.5 H,-5 °C
    标题:The Objective Of This Paper Is To Study The Synthetic Technology Of (2S,3R)-1-Dimethylamino-3-(3-Methoxyphenyl)-2-Methylpentan-3-Ol
    作者:Xie,Ying; Et Al
    参考文献:Xiandai Yaowu Yu Linchuang 日期:2011 卷标:26(6) 页码:461-463]

    51690-03-0 = 809282-20-0
    反应条件:1.1 Reagents: O,O′-Dibenzoyl-(2R,3R)-Tartaric Acid Monohydrate Solvents: Methanol; Overnight,40 °C; 40 °C -> Rt; 5 H,Rt1.2 Reagents: Sodium Hydroxide Solvents: 2-Methyltetrahydrofuran,Water; Ph 9 - 10,Rt2.1 Reagents: Sulfuric Acid Magnesium Salt (1:1) Solvents: Tetrahydrofuran; Rt; 1 H,Reflux; Reflux -> 5 °C2.2 Solvents: Tetrahydrofuran; 5 °C; 1 H,5 °C2.3 Reagents: Acetic Acid Solvents: Water; 5 °C; 30 Min,5 °C2.4 Reagents: Ammonia Solvents: Water; 5 °C; 10 Min,5 °C
    标题:Synthesis Of Tapentadol Hydrochloride
    作者:Cheng,Qing-Fang; Et Al
    参考文献:Zhongguo Xinyao Zazhi 日期:2013 卷标:22(14) 页码:1691-1693]

    51690-03-0 + 2743-38-6 = 809282-20-0
    反应条件:1.1 Solvents: Methanol,Water; Reflux2.1 Reagents: Sodium Hydroxide Solvents: Dichloromethane,Water; Ph 9,0 °C3.1 Reagents: Magnesium Solvents: Tetrahydrofuran; 30 °C; Reflux; 1 H,Reflux; Reflux -> 5 °C3.2 Solvents: Tetrahydrofuran; 5 °C; 17 H,30 °C; 30 °C -> -5 °C3.3 Reagents: Ammonium Chloride Solvents: Water; -5 - 0 °C; 0.5 H,-5 °C
    标题:The Objective Of This Paper Is To Study The Synthetic Technology Of (2S,3R)-1-Dimethylamino-3-(3-Methoxyphenyl)-2-Methylpentan-3-Ol
    作者:Xie,Ying; Et Al
    参考文献:Xiandai Yaowu Yu Linchuang 日期:2011 卷标:26(6) 页码:461-463
📜(S)-3-(二甲基氨基)-1-(3-甲氧基苯基)-2-甲基-1-丙酮置于magnesium,硫酸氢铵,水体系中,用 乙醚 作为反应溶剂,化学反应 4.5H,以98%的收率获得产物(2S,3R)-1-(二甲基氨基)-3-(3-甲氧基苯基)-2-甲基-3-戊醇
参考文献:Wo2008/12047
标题:Wo2008/12047

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专利信息


专利号:US-2013296608-A1
优先权日:2011-01-27
标 题 :Novel stereospecific synthesis of (-) (2s, 3s)-1-dimethylamino-3-(3-methoxyphenyl)-2-methyl pentan-3-ol
发明人：MOHAN RAO DODDA; KRISHNAREDDY PINGILI; RAMACHANDRAREDDY PINGILI; HARITHA KIRLA; SRINIVAS KOLLURU
权利人:MOHAN RAO DODDA; KRISHNAREDDY PINGILI; RAMACHANDRAREDDY PINGILI; HARITHA KIRLA; SRINIVAS KOLLURU; SYMED LABS LTD
摘要:The present invention relates to a novel stereospecific synthesis of (−)(2S,3S)-1-dimethylamino-3-(3-methoxyphenyl)-2-methyl pentan-3-ol an intermediate in the synthesis of 3-[(1R,2R)-3-(dimethylamino)-1-ethyl-2-methylpropyl]phenol.

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合成参考文献


摘要:Kleemann, A.; Engel, J.; Kutscher, B.; Reichert, D., Pharmaceutical Substances[Online], Thieme: Stuttgart, (2010).
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