3-Cbz-3,6-二氮杂双环[3.2.0]庚烷合成路线 （共 8 条）
反应条件
1: sodium hydroxide / ethanol; water / 0.67 h / 20 °C 2: hydrogen / 5 Pd(II)/C(eggshell) / methanol / 1.5 h / 775.74 Torr View Scheme
参考文献
JANSSEN PHARMACEUTICA NV; BRANSTETTER, Bryan, James; LETAVIC, Michael, A.; LY, Kiev, S.; RUDOLPH, Dale, A.; SAVALL, Brad, M.; SHAH, Chandravadan, R.; SHIREMAN, Brock, T.
Patent: WO2011/50202 A1, 2011 ;
WO 2011/050202 A1
反应条件
1.1: trifluoroacetic acid / dichloromethane / 20 h
1.2: pH ~ 12
2.1: sodium hydroxide / ethanol; water / 1.5 h / 60 °C
View Scheme
参考文献
JANSSEN PHARMACEUTICA NV; BRANSTETTER, Bryan, James; LETAVIC, Michael, A.; LY, Kiev, S.; RUDOLPH, Dale, A.; SAVALL, Brad, M.; SHAH, Chandravadan, R.; SHIREMAN, Brock, T.
Patent: WO2011/50200 A1, 2011 ;
WO 2011/050200 A1
反应条件
1.1: sodium hydroxide / toluene; water / 4 h / 0 - 20 °C / Inert atmosphere
2.1: potassium hydroxide / N-benzyl-N,N,N-triethylammonium chloride / toluene / 48 h / 50 °C / Inert atmosphere
3.1: formic acid / 20 °C / Inert atmosphere
4.1: hydroxylamine hydrochloride; sodium acetate / acetonitrile; water / 20 °C / Inert atmosphere
5.1: pentan-1-ol / 20 h / 135 °C / Inert atmosphere
5.2: Raney Ni / 4 h / 3102.97 Torr
6.1: sodium hydrogencarbonate / ethanol; water; pentan-1-ol / 15 h / 20 °C / Inert atmosphere
7.1: triethylamine / dichloromethane / 22.33 h / 0 - 20 °C / Inert atmosphere
8.1: trifluoroacetic acid / dichloromethane / 20 h
8.2: pH ~ 12
9.1: sodium hydroxide / ethanol; water / 1.5 h / 60 °C
View Scheme
参考文献
JANSSEN PHARMACEUTICA NV; BRANSTETTER, Bryan, James; LETAVIC, Michael, A.; LY, Kiev, S.; RUDOLPH, Dale, A.; SAVALL, Brad, M.; SHAH, Chandravadan, R.; SHIREMAN, Brock, T.
Patent: WO2011/50200 A1, 2011 ;
WO 2011/050200 A1
反应条件
1.1: potassium hydroxide / N-benzyl-N,N,N-triethylammonium chloride / toluene / 48 h / 50 °C / Inert atmosphere
2.1: formic acid / 20 °C / Inert atmosphere
3.1: hydroxylamine hydrochloride; sodium acetate / acetonitrile; water / 20 °C / Inert atmosphere
4.1: pentan-1-ol / 20 h / 135 °C / Inert atmosphere
4.2: Raney Ni / 4 h / 3102.97 Torr
5.1: sodium hydrogencarbonate / ethanol; water; pentan-1-ol / 15 h / 20 °C / Inert atmosphere
6.1: triethylamine / dichloromethane / 22.33 h / 0 - 20 °C / Inert atmosphere
7.1: trifluoroacetic acid / dichloromethane / 20 h
7.2: pH ~ 12
8.1: sodium hydroxide / ethanol; water / 1.5 h / 60 °C
View Scheme
参考文献
JANSSEN PHARMACEUTICA NV; BRANSTETTER, Bryan, James; LETAVIC, Michael, A.; LY, Kiev, S.; RUDOLPH, Dale, A.; SAVALL, Brad, M.; SHAH, Chandravadan, R.; SHIREMAN, Brock, T.
Patent: WO2011/50200 A1, 2011 ;
WO 2011/050200 A1
反应条件
1.1: formic acid / 20 °C / Inert atmosphere
2.1: hydroxylamine hydrochloride; sodium acetate / acetonitrile; water / 20 °C / Inert atmosphere
3.1: pentan-1-ol / 20 h / 135 °C / Inert atmosphere
3.2: Raney Ni / 4 h / 3102.97 Torr
4.1: sodium hydrogencarbonate / ethanol; water; pentan-1-ol / 15 h / 20 °C / Inert atmosphere
5.1: triethylamine / dichloromethane / 22.33 h / 0 - 20 °C / Inert atmosphere
6.1: trifluoroacetic acid / dichloromethane / 20 h
6.2: pH ~ 12
7.1: sodium hydroxide / ethanol; water / 1.5 h / 60 °C
View Scheme
参考文献
JANSSEN PHARMACEUTICA NV; BRANSTETTER, Bryan, James; LETAVIC, Michael, A.; LY, Kiev, S.; RUDOLPH, Dale, A.; SAVALL, Brad, M.; SHAH, Chandravadan, R.; SHIREMAN, Brock, T.
Patent: WO2011/50200 A1, 2011 ;
WO 2011/050200 A1
反应条件
1.1: pentan-1-ol / 20 h / 135 °C / Inert atmosphere
1.2: Raney Ni / 4 h / 3102.97 Torr
2.1: sodium hydrogencarbonate / ethanol; water; pentan-1-ol / 15 h / 20 °C / Inert atmosphere
3.1: triethylamine / dichloromethane / 22.33 h / 0 - 20 °C / Inert atmosphere
4.1: trifluoroacetic acid / dichloromethane / 20 h
4.2: pH ~ 12
5.1: sodium hydroxide / ethanol; water / 1.5 h / 60 °C
View Scheme
参考文献
JANSSEN PHARMACEUTICA NV; BRANSTETTER, Bryan, James; LETAVIC, Michael, A.; LY, Kiev, S.; RUDOLPH, Dale, A.; SAVALL, Brad, M.; SHAH, Chandravadan, R.; SHIREMAN, Brock, T.
Patent: WO2011/50200 A1, 2011 ;
WO 2011/050200 A1
反应条件
1.1: sodium hydrogencarbonate / ethanol; water; pentan-1-ol / 15 h / 20 °C / Inert atmosphere
2.1: triethylamine / dichloromethane / 22.33 h / 0 - 20 °C / Inert atmosphere
3.1: trifluoroacetic acid / dichloromethane / 20 h
3.2: pH ~ 12
4.1: sodium hydroxide / ethanol; water / 1.5 h / 60 °C
View Scheme
参考文献
JANSSEN PHARMACEUTICA NV; BRANSTETTER, Bryan, James; LETAVIC, Michael, A.; LY, Kiev, S.; RUDOLPH, Dale, A.; SAVALL, Brad, M.; SHAH, Chandravadan, R.; SHIREMAN, Brock, T.
Patent: WO2011/50200 A1, 2011 ;
WO 2011/050200 A1
反应条件
1.1: triethylamine / dichloromethane / 22.33 h / 0 - 20 °C / Inert atmosphere
2.1: trifluoroacetic acid / dichloromethane / 20 h
2.2: pH ~ 12
3.1: sodium hydroxide / ethanol; water / 1.5 h / 60 °C
View Scheme
参考文献
JANSSEN PHARMACEUTICA NV; BRANSTETTER, Bryan, James; LETAVIC, Michael, A.; LY, Kiev, S.; RUDOLPH, Dale, A.; SAVALL, Brad, M.; SHAH, Chandravadan, R.; SHIREMAN, Brock, T.
Patent: WO2011/50200 A1, 2011 ;
WO 2011/050200 A1
