(2S,3aR,7aS)-八氢吲哚-2-甲酸苄酯盐酸盐合成路线 （共 13 条）
反应条件
thionyl chloride in dichloromethane
参考文献
ABBOTT LABORATORIES; CHEMBURKAR, Sanjay, R.; REDDY, Rajarathman, E.; REAMER, Douglas, M.; PAVLINA, John, T.; ULREY, Stephen, S.; KOTECKI, Brian, J.
Patent: WO2011/9021 A1, 2011 ;
Location in patent: Page/Page column 39-40 ;
反应条件
hydrogenchloride in acetone T=0 - 10°C; pH=2; 0.333333 - 0.5 h;
参考文献
WO2006/14916 A2, ;
Page/Page column 10-11 ;
反应条件
1: With sodium hydroxide in water 1 h; 2: With (2R,3S)-(-)-di-O-benzoyl tartaric acid in methanol 1 h; Resolution of racemate; 3: With hydrogenchloride; sodium hydroxide more than 3 stages;
参考文献
EP1724260 A1, ;
Page/Page column 14 ;
反应条件
1.1: ytterbium(III) triflate / n-heptane / 3 h / Reflux 2.1: sodium tetrahydroborate; acetic acid / acetonitrile / 2 - 22 °C / Inert atmosphere 2.2: pH ~ 8 3.1: sodium t-butanolate / tert-butyl alcohol; tetrahydrofuran / 5 h / 6 - 22 °C / Inert atmosphere 4.1: lithium borohydride / tetrahydrofuran / 12 h / 15 °C / Reflux; Inert atmosphere 4.2: 0.5 h / 5 - 15 °C 4.3: pH ~ 8.7 5.1: sodium carbonate / acetonitrile / 18 h / Reflux; Inert atmosphere 6.1: triethylamine / dichloromethane / 1.42 h / 2 - 22 °C / Inert atmosphere 7.1: sodium t-butanolate / tetrahydrofuran / 1 h / 19 - 65 °C / Inert atmosphere 8.1: hydrogen / 5 Pd(II)/C(eggshell) / ethanol / 3 h / 60 °C / 749.88 Torr 9.1: hydrogenchloride; water / 4 h / Reflux 10.1: thionyl chloride / dichloromethane View Scheme
反应条件
1.1: sodium tetrahydroborate; acetic acid / acetonitrile / 2 - 22 °C / Inert atmosphere 1.2: pH ~ 8 2.1: sodium t-butanolate / tert-butyl alcohol; tetrahydrofuran / 5 h / 6 - 22 °C / Inert atmosphere 3.1: lithium borohydride / tetrahydrofuran / 12 h / 15 °C / Reflux; Inert atmosphere 3.2: 0.5 h / 5 - 15 °C 3.3: pH ~ 8.7 4.1: sodium carbonate / acetonitrile / 18 h / Reflux; Inert atmosphere 5.1: triethylamine / dichloromethane / 1.42 h / 2 - 22 °C / Inert atmosphere 6.1: sodium t-butanolate / tetrahydrofuran / 1 h / 19 - 65 °C / Inert atmosphere 7.1: hydrogen / 5 Pd(II)/C(eggshell) / ethanol / 3 h / 60 °C / 749.88 Torr 8.1: hydrogenchloride; water / 4 h / Reflux 9.1: thionyl chloride / dichloromethane View Scheme
反应条件
1: sodium carbonate / acetonitrile / 18 h / Reflux; Inert atmosphere 2: triethylamine / dichloromethane / 1.42 h / 2 - 22 °C / Inert atmosphere 3: sodium t-butanolate / tetrahydrofuran / 1 h / 19 - 65 °C / Inert atmosphere 4: hydrogen / 5 Pd(II)/C(eggshell) / ethanol / 3 h / 60 °C / 749.88 Torr 5: hydrogenchloride; water / 4 h / Reflux 6: thionyl chloride / dichloromethane View Scheme
反应条件
1: triethylamine / dichloromethane / 1.42 h / 2 - 22 °C / Inert atmosphere 2: sodium t-butanolate / tetrahydrofuran / 1 h / 19 - 65 °C / Inert atmosphere 3: hydrogen / 5 Pd(II)/C(eggshell) / ethanol / 3 h / 60 °C / 749.88 Torr 4: hydrogenchloride; water / 4 h / Reflux 5: thionyl chloride / dichloromethane View Scheme
反应条件
1: sodium t-butanolate / tetrahydrofuran / 1 h / 19 - 65 °C / Inert atmosphere 2: hydrogen / 5 Pd(II)/C(eggshell) / ethanol / 3 h / 60 °C / 749.88 Torr 3: hydrogenchloride; water / 4 h / Reflux 4: thionyl chloride / dichloromethane View Scheme
反应条件
1: hydrogen / 5 Pd(II)/C(eggshell) / ethanol / 3 h / 60 °C / 749.88 Torr 2: hydrogenchloride; water / 4 h / Reflux 3: thionyl chloride / dichloromethane View Scheme
反应条件
1.1: sodium t-butanolate / tert-butyl alcohol; tetrahydrofuran / 5 h / 6 - 22 °C / Inert atmosphere 2.1: lithium borohydride / tetrahydrofuran / 12 h / 15 °C / Reflux; Inert atmosphere 2.2: 0.5 h / 5 - 15 °C 2.3: pH ~ 8.7 3.1: sodium carbonate / acetonitrile / 18 h / Reflux; Inert atmosphere 4.1: triethylamine / dichloromethane / 1.42 h / 2 - 22 °C / Inert atmosphere 5.1: sodium t-butanolate / tetrahydrofuran / 1 h / 19 - 65 °C / Inert atmosphere 6.1: hydrogen / 5 Pd(II)/C(eggshell) / ethanol / 3 h / 60 °C / 749.88 Torr 7.1: hydrogenchloride; water / 4 h / Reflux 8.1: thionyl chloride / dichloromethane View Scheme
