N-叔丁氧羰基-4-哌啶酮合成路线 （共 500 条）
反应条件
1.1: potassium hydroxide; iodine / 2.5 h / 0 - 20 °C 2.1: potassium tert-butylate / tetrahydrofuran / 0.33 h / 0 °C 2.2: 0 - 20 °C 3.1: hydrogenchloride / 1,4-dioxane / 50 °C 3.2: pH 10 3.3: 4 h View Scheme
参考文献
CONVERGENCE PHARMACEUTICALS LIMITED; WITTY, David R.; NORTON, David; TIERNEY, Jason Paul; LORTHIOIR, Ghislaine; SIME, Mairi; PHILPOTT, Karen Louise
Patent: WO2012/80735 A1, 2012 ;
WO 2012/080735 A1
反应条件
1: HCl; AcOH
2: HCl
3: NaOH
View Scheme
参考文献
Chen, Jian Jeffrey; Dewdney, Nolan; Lin, Xiaohong; Martin, Robert L.; Walker, Keith A. M.; Huang, Jane; Chu, Frances; Eugui, Elsie; Mirkovich, Anna; Kim, Yong; Sarma, Keshab; Arzeno, Humberto; Van Wart, Harold E.
Bioorganic and Medicinal Chemistry Letters, 2003 , vol. 13, # 22 p. 3951 - 3954
反应条件
1: propynoic acid ethyl ester With n-butyllithium in tetrahydrofuran
T=-78°C;
2: tert-butyl 4-oxo-piperidine-1-carboxylate in tetrahydrofuran
T=-78°C; 1 h;
参考文献
MERCK SHARP and DOHME LIMITED
Patent: WO2004/78750 A1, 2004 ;
Location in patent: Page 78-79 ;
WO 2004/078750 A1
反应条件
1.1: n-BuLi / tetrahydrofuran / -78 °C
1.2: tetrahydrofuran / 1 h / -78 °C
2.1: H2 / Pd/C / ethanol
3.1: p-TsOH / toluene / 3 h / Heating
4.1: DIBAL-H / CH2Cl2 / 5 h / -78 - 0 °C
View Scheme
参考文献
Cooper, Laura C.; Carlson, Emma J.; Castro, Jose L.; Chicchi, Gary G.; Dinnell, Kevin; Di Salvo, Jerry; Elliott, Jason M.; Hollingworth, Gregory J.; Kurtz, Marc M.; Ridgill, Mark P.; Rycroft, Wayne; Tsao, Kwei-Lan; Swain, Christopher J.
Bioorganic and Medicinal Chemistry Letters, 2002 , vol. 12, # 13 p. 1759 - 1762
反应条件
1: bromine / dichloromethane / 2 h / 20 °C
2: N,N-dimethyl-formamide / 6 h / 60 °C
View Scheme
参考文献
SANOFI
Patent: US2012/245149 A1, 2012 ;
反应条件
1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 0 - 20 °C
2: potassium carbonate / methanol / 12 h / 20 °C
3: dichloromethane / 0.5 h / 20 °C
View Scheme
参考文献
EXELIXIS, INC.; RICE, Kenneth
Patent: WO2012/71509 A2, 2012 ;
WO 2012/071509 A2
反应条件
1.1: tetrahydrofuran; diethyl ether / 18 h / 0 - 23 °C
2.1: potassium carbonate / N,N-dimethyl-formamide / 18 h / 0 - 23 °C
3.1: RuCl2(tricyclohexylphosphine)2(benzylidene) / dichloromethane / 18 h / 0 - 23 °C
4.1: borane-THF / tetrahydrofuran / 18 h / 0 °C
4.2: 1 h / 0 - 23 °C
View Scheme
参考文献
Cernak, Timothy; Dykstra, Kevin; Levorse, Dorothy; Verras, Andreas; Balkovec, James; Nargund, Ravi; DeVita, Robert
Tetrahedron Letters, 2011 , vol. 52, # 48 p. 6457 - 6459
反应条件
1.1: n-BuLi / tetrahydrofuran / -78 °C
1.2: tetrahydrofuran / 1 h / -78 °C
2.1: H2 / Pd/C / ethanol
View Scheme
参考文献
Cooper, Laura C.; Carlson, Emma J.; Castro, Jose L.; Chicchi, Gary G.; Dinnell, Kevin; Di Salvo, Jerry; Elliott, Jason M.; Hollingworth, Gregory J.; Kurtz, Marc M.; Ridgill, Mark P.; Rycroft, Wayne; Tsao, Kwei-Lan; Swain, Christopher J.
Bioorganic and Medicinal Chemistry Letters, 2002 , vol. 12, # 13 p. 1759 - 1762
反应条件
1: With acetic acid in dichloromethane
T=20°C; 3 h;
2: With sodium tris(acetoxy)borohydride in dichloromethane
T=20°C; 18 h;
参考文献
GLAXOSMITHKLINE LLC; BROOKS, Carl, A.; CHEUNG, Mui; EIDAM, Hilary, S.; FOX, Ryan, M.; HILFIKER, Mark, A.; MANAS, Eric, S.; YE, Guosen
Patent: WO2011/119701 A1, 2011 ;
Location in patent: Page/Page column 38 ;
WO 2011/119701 A1
反应条件
1: in anhydrous dichloroethane
T=20°C; 0.5 h;
2: With sodium tris(acetoxy)borohydride in anhydrous dichloroethane
T=20°C; 18 h;
参考文献
F. HOFFMANN-LA ROCHE AG
Patent: WO2009/53715 A1, 2009 ;
Location in patent: Page/Page column 77-78 ;
WO 2009/053715 A1
