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乙二醇
甲醛
63148-62-9
MDI
丁酮
二甲基亚砜
碳酸氢钠
471-34-1
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乙二醇
甲醛
63148-62-9
MDI
丁酮
二甲基亚砜
碳酸氢钠
471-34-1
外消旋5-羧基托特罗定
合成路线
（共 16 条）
214601-12-4
3-[(1R)-3-[二(1-甲基乙基)氨基]-1-苯基丙基]-4-羟基-苯甲醛
→
反应条件
1076199-77-3
外消旋5-羧基托特罗定
反应条件
hydrogen; 5 palladium on charcoal in methanol T=25 - 30°C; P=2206.72 - 2942.29 Torr; 8 h; autoclave;
参考文献
MSN LABORATORIES LIMITED; SATYANARAYANA REDDY, Manne; THIRUMALAI RAJAN, Srinivasan; ESWARAIAH, Sajja; RAGHURAM, Suraparaju; SEETHA RAMA SARMA, Peri
Patent: WO2012/98560 A2, 2012 ;
Location in patent: Page/Page column 66 ;
WO 2012/098560 A2
87462-12-2
N,N-二异丙基-3-苯基-2-丙烯胺
+
99-96-7
对羟基苯甲酸
→
反应条件
1076199-77-3
外消旋5-羧基托特罗定
反应条件
sulfuric acid; acetic acid in n-heptane T=80 - 85°C;
参考文献
Ragactives, S.L.U.
Patent: EP2281801 A1, 2011 ;
Location in patent: Page/Page column 15-16 ;
106-41-2
4-溴苯酚
→
反应条件
1076199-77-3
外消旋5-羧基托特罗定
反应条件
1.1: sulfuric acid / 12 h / 120 - 125 °C 2.1: potassium carbonate; sodium iodide / acetone / 25 - 30 °C 2.2: 5.5 h / 15 °C / Reflux 3.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 4 h / 5 - 10 °C / Inert atmosphere 4.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 2 h / 0 - 5 °C 5.1: acetonitrile / 32 h / 95 - 100 °C / autoclave; Inert atmosphere 6.1: n-butyllithium / tetrahydrofuran / 0.75 h / -65 - -55 °C 7.1: (2S,3S)-2,3-dihydroxybutanedioic acid / isopropyl alcohol / 16 h / 30 - 35 °C 7.2: 10 - 15 °C 8.1: hydrogen / 5 palladium on charcoal / methanol / 8 h / 25 - 30 °C / 2206.72 - 2942.29 Torr / autoclave 9.1: hydrogen / 5 palladium on charcoal / methanol / 8 h / 25 - 30 °C / 2206.72 - 2942.29 Torr / autoclave View Scheme
参考文献
MSN LABORATORIES LIMITED; SATYANARAYANA REDDY, Manne; THIRUMALAI RAJAN, Srinivasan; ESWARAIAH, Sajja; RAGHURAM, Suraparaju; SEETHA RAMA SARMA, Peri
Patent: WO2012/98560 A2, 2012 ;
WO 2012/098560 A2
621-82-9
肉桂酸
→
反应条件
1076199-77-3
外消旋5-羧基托特罗定
反应条件
1.1: sulfuric acid / 12 h / 120 - 125 °C 2.1: potassium carbonate; sodium iodide / acetone / 25 - 30 °C 2.2: 5.5 h / 15 °C / Reflux 3.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 4 h / 5 - 10 °C / Inert atmosphere 4.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 2 h / 0 - 5 °C 5.1: acetonitrile / 32 h / 95 - 100 °C / autoclave; Inert atmosphere 6.1: n-butyllithium / tetrahydrofuran / 0.75 h / -65 - -55 °C 7.1: (2S,3S)-2,3-dihydroxybutanedioic acid / isopropyl alcohol / 16 h / 30 - 35 °C 7.2: 10 - 15 °C 8.1: hydrogen / 5 palladium on charcoal / methanol / 8 h / 25 - 30 °C / 2206.72 - 2942.29 Torr / autoclave 9.1: hydrogen / 5 palladium on charcoal / methanol / 8 h / 25 - 30 °C / 2206.72 - 2942.29 Torr / autoclave View Scheme
参考文献
MSN LABORATORIES LIMITED; SATYANARAYANA REDDY, Manne; THIRUMALAI RAJAN, Srinivasan; ESWARAIAH, Sajja; RAGHURAM, Suraparaju; SEETHA RAMA SARMA, Peri
Patent: WO2012/98560 A2, 2012 ;
WO 2012/098560 A2
156755-23-6
6-溴-3,4-二氢-4-苯基-2H-1-苯并吡喃-2-酮
→
反应条件
1076199-77-3
外消旋5-羧基托特罗定
反应条件
1.1: potassium carbonate; sodium iodide / acetone / 25 - 30 °C 1.2: 5.5 h / 15 °C / Reflux 2.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 4 h / 5 - 10 °C / Inert atmosphere 3.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 2 h / 0 - 5 °C 4.1: acetonitrile / 32 h / 95 - 100 °C / autoclave; Inert atmosphere 5.1: n-butyllithium / tetrahydrofuran / 0.75 h / -65 - -55 °C 6.1: (2S,3S)-2,3-dihydroxybutanedioic acid / isopropyl alcohol / 16 h / 30 - 35 °C 6.2: 10 - 15 °C 7.1: hydrogen / 5 palladium on charcoal / methanol / 8 h / 25 - 30 °C / 2206.72 - 2942.29 Torr / autoclave 8.1: hydrogen / 5 palladium on charcoal / methanol / 8 h / 25 - 30 °C / 2206.72 - 2942.29 Torr / autoclave View Scheme
参考文献
MSN LABORATORIES LIMITED; SATYANARAYANA REDDY, Manne; THIRUMALAI RAJAN, Srinivasan; ESWARAIAH, Sajja; RAGHURAM, Suraparaju; SEETHA RAMA SARMA, Peri
Patent: WO2012/98560 A2, 2012 ;
WO 2012/098560 A2
156755-24-7
(±)-5-溴-b-苯基-2-(苯基甲氧基)-苯丙酸甲酯
→
反应条件
1076199-77-3
外消旋5-羧基托特罗定
反应条件
1.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 4 h / 5 - 10 °C / Inert atmosphere 2.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 2 h / 0 - 5 °C 3.1: acetonitrile / 32 h / 95 - 100 °C / autoclave; Inert atmosphere 4.1: n-butyllithium / tetrahydrofuran / 0.75 h / -65 - -55 °C 5.1: (2S,3S)-2,3-dihydroxybutanedioic acid / isopropyl alcohol / 16 h / 30 - 35 °C 5.2: 10 - 15 °C 6.1: hydrogen / 5 palladium on charcoal / methanol / 8 h / 25 - 30 °C / 2206.72 - 2942.29 Torr / autoclave 7.1: hydrogen / 5 palladium on charcoal / methanol / 8 h / 25 - 30 °C / 2206.72 - 2942.29 Torr / autoclave View Scheme
参考文献
MSN LABORATORIES LIMITED; SATYANARAYANA REDDY, Manne; THIRUMALAI RAJAN, Srinivasan; ESWARAIAH, Sajja; RAGHURAM, Suraparaju; SEETHA RAMA SARMA, Peri
Patent: WO2012/98560 A2, 2012 ;
WO 2012/098560 A2
250214-37-0
→
反应条件
1076199-77-3
外消旋5-羧基托特罗定
反应条件
1.1: acetonitrile / 32 h / 95 - 100 °C / autoclave; Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran / 0.75 h / -65 - -55 °C 3.1: (2S,3S)-2,3-dihydroxybutanedioic acid / isopropyl alcohol / 16 h / 30 - 35 °C 3.2: 10 - 15 °C 4.1: hydrogen / 5 palladium on charcoal / methanol / 8 h / 25 - 30 °C / 2206.72 - 2942.29 Torr / autoclave 5.1: hydrogen / 5 palladium on charcoal / methanol / 8 h / 25 - 30 °C / 2206.72 - 2942.29 Torr / autoclave View Scheme
参考文献
MSN LABORATORIES LIMITED; SATYANARAYANA REDDY, Manne; THIRUMALAI RAJAN, Srinivasan; ESWARAIAH, Sajja; RAGHURAM, Suraparaju; SEETHA RAMA SARMA, Peri
Patent: WO2012/98560 A2, 2012 ;
WO 2012/098560 A2
156755-35-0
3-[(1R)-3-[双(1-甲基乙基)氨基]-1-苯基丙基]-4-(苯基甲氧基)苯甲酸甲酯
→
反应条件
1076199-77-3
外消旋5-羧基托特罗定
反应条件
1: hydrogen / 5 palladium on charcoal / ethyl acetate / 18 h / 25 - 30 °C / 2206.72 - 2942.29 Torr / autoclave 2: diisobutylaluminium hydride / toluene / 1 h / -78 °C / Inert atmosphere 3: hydrogen / 5 palladium on charcoal / methanol / 8 h / 25 - 30 °C / 2206.72 - 2942.29 Torr / autoclave View Scheme
参考文献
MSN LABORATORIES LIMITED; SATYANARAYANA REDDY, Manne; THIRUMALAI RAJAN, Srinivasan; ESWARAIAH, Sajja; RAGHURAM, Suraparaju; SEETHA RAMA SARMA, Peri
Patent: WO2012/98560 A2, 2012 ;
WO 2012/098560 A2
286930-05-0
4-(苄氧基)-3-(3-(二异丙基氨基)-1-苯基丙基)苯甲酸甲酯
→
反应条件
1076199-77-3
外消旋5-羧基托特罗定
反应条件
1: isopropyl alcohol / 2 h / 80 - 85 °C 2: sodium carbonate / water / 25 - 30 °C / pH 9.5 3: hydrogen / 5 palladium on charcoal / ethyl acetate / 18 h / 25 - 30 °C / 2206.72 - 2942.29 Torr / autoclave 4: diisobutylaluminium hydride / toluene / 1 h / -78 °C / Inert atmosphere 5: hydrogen / 5 palladium on charcoal / methanol / 8 h / 25 - 30 °C / 2206.72 - 2942.29 Torr / autoclave View Scheme
参考文献
MSN LABORATORIES LIMITED; SATYANARAYANA REDDY, Manne; THIRUMALAI RAJAN, Srinivasan; ESWARAIAH, Sajja; RAGHURAM, Suraparaju; SEETHA RAMA SARMA, Peri
Patent: WO2012/98560 A2, 2012 ;
WO 2012/098560 A2
837376-33-7
→
反应条件
1076199-77-3
外消旋5-羧基托特罗定
反应条件
1.1: (2S,3S)-2,3-dihydroxybutanedioic acid / isopropyl alcohol / 16 h / 30 - 35 °C 1.2: 10 - 15 °C 2.1: hydrogen / 5 palladium on charcoal / methanol / 8 h / 25 - 30 °C / 2206.72 - 2942.29 Torr / autoclave 3.1: hydrogen / 5 palladium on charcoal / methanol / 8 h / 25 - 30 °C / 2206.72 - 2942.29 Torr / autoclave View Scheme
参考文献
MSN LABORATORIES LIMITED; SATYANARAYANA REDDY, Manne; THIRUMALAI RAJAN, Srinivasan; ESWARAIAH, Sajja; RAGHURAM, Suraparaju; SEETHA RAMA SARMA, Peri
Patent: WO2012/98560 A2, 2012 ;
WO 2012/098560 A2
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