3,8-二氮杂双环[4.2.0]辛烷-3-羧酸叔丁酯合成路线 （共 6 条）
反应条件
hydrogen; 20 palladium hydroxide on carbon in ethanol
T=50°C; P=3102.97 Torr; 48 h;
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 ;
Location in patent: Page/Page column 46 ;
WO 2011/050202 A1
反应条件
1.1: triethylamine; hydrogen / 20 palladium hydroxide on carbon / ethanol / 24 h / 3102.97 Torr
2.1: toluene / 72 h / Reflux; Dean-Stark apparatus
3.1: acetic acid; sodium tris(acetoxy)borohydride / toluene / 16 h / 5 - 20 °C / Molecular sieve
4.1: lithium aluminium tetrahydride / tetrahydrofuran / 2.25 h / 0 - 20 °C
4.2: 16 h / 0 °C
5.1: triethylamine / tetrahydrofuran / 1 h / 0 - 20 °C
6.1: caesium carbonate / tetrahydrofuran / 18 h / 60 °C
7.1: hydrogen / 20 palladium hydroxide on carbon / ethanol / 48 h / 50 °C / 3102.97 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: WO2011/50200 A1, 2011 ;
WO 2011/050200 A1
反应条件
1.1: toluene / 72 h / Reflux; Dean-Stark apparatus
2.1: acetic acid; sodium tris(acetoxy)borohydride / toluene / 16 h / 5 - 20 °C / Molecular sieve
3.1: lithium aluminium tetrahydride / tetrahydrofuran / 2.25 h / 0 - 20 °C
3.2: 16 h / 0 °C
4.1: triethylamine / tetrahydrofuran / 1 h / 0 - 20 °C
5.1: caesium carbonate / tetrahydrofuran / 18 h / 60 °C
6.1: hydrogen / 20 palladium hydroxide on carbon / ethanol / 48 h / 50 °C / 3102.97 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: WO2011/50200 A1, 2011 ;
WO 2011/050200 A1
反应条件
1.1: triethylamine; hydrogen / 20 palladium hydroxide on carbon / ethanol / 24 h / 3102.97 Torr
2.1: toluene / 72 h / Reflux; Dean-Stark apparatus
3.1: acetic acid; sodium tris(acetoxy)borohydride / toluene / 16 h / 5 - 20 °C / Molecular sieve
4.1: lithium aluminium tetrahydride / tetrahydrofuran / 2.25 h / 0 - 20 °C
4.2: 16 h / 0 °C
5.1: triethylamine / tetrahydrofuran / 1 h / 0 - 20 °C
6.1: caesium carbonate / tetrahydrofuran / 18 h / 60 °C
7.1: hydrogen / 20 palladium hydroxide on carbon / ethanol / 48 h / 50 °C / 3102.97 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: WO2011/50200 A1, 2011 ;
WO 2011/050200 A1
反应条件
1.1: acetic acid; sodium tris(acetoxy)borohydride / toluene / 16 h / 5 - 20 °C / Molecular sieve
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 2.25 h / 0 - 20 °C
2.2: 16 h / 0 °C
3.1: triethylamine / tetrahydrofuran / 1 h / 0 - 20 °C
4.1: caesium carbonate / tetrahydrofuran / 18 h / 60 °C
5.1: hydrogen / 20 palladium hydroxide on carbon / ethanol / 48 h / 50 °C / 3102.97 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: WO2011/50200 A1, 2011 ;
WO 2011/050200 A1
反应条件
1.1: lithium aluminium tetrahydride / tetrahydrofuran / 2.25 h / 0 - 20 °C
1.2: 16 h / 0 °C
2.1: triethylamine / tetrahydrofuran / 1 h / 0 - 20 °C
3.1: caesium carbonate / tetrahydrofuran / 18 h / 60 °C
4.1: hydrogen / 20 palladium hydroxide on carbon / ethanol / 48 h / 50 °C / 3102.97 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: WO2011/50200 A1, 2011 ;
WO 2011/050200 A1
