(R)-(-)-3-奎宁醇合成路线 （共 33 条）
反应条件
2: 80 percent / 2.5N aq. NaOH / 1 h / 50 °C View Scheme
参考文献
Synthetic Communications, , vol. 22, # 13 p. 1895 - 1911
反应条件
horse serum butyrycholinesterase; water in phosphate buffer T=30°C; pH=7.4; Enzyme kinetics;
参考文献
Journal of Physical Organic Chemistry, , vol. 15, # 8 p. 608 - 614
反应条件
sodium hydride in toluene 3 h; Heating;
参考文献
Naito, Ryo; Yonetoku, Yasuhiro; Okamoto, Yoshinori; Toyoshima, Akira; Ikeda, Ken; Takeuchi, Makoto
Journal of Medicinal Chemistry, 2005 , vol. 48, # 21 p. 6597 - 6606
反应条件
sodium hydride in N,N-dimethyl acetamide T=0 - 60°C;
参考文献
TEVA PHARMACEUTICAL INDUSTRIES LTD.; TEVA PHARMACEUTICALS USA, INC.
Patent: WO2007/76116 A2, 2007 ;
Location in patent: Page/Page column 13 ;
反应条件
1: (3R)-3-hydroxy-1-azabicyclo[2.2.2]octane With 18-crown-6 ether; sodium hydride in toluene; mineral oil Inert atmosphere; 2: 4-nitrophenyl (1S)-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate in toluene; mineral oil T=20 - 110°C; 18 h; Inert atmosphere;
参考文献
Wang, Sa; Onaran, M. Burak; Seto, Christopher T.
Organic Letters, 2010 , vol. 12, # 12 p. 2690 - 2693
反应条件
1: (3R)-3-hydroxy-1-azabicyclo[2.2.2]octane With sodium methylate in toluene T=5°C; Inert atmosphereReflux; 2: (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline in N,N-dimethyl-formamide; toluene T=60°C; Reflux;
参考文献
CADILA HEALTHCARE LIMITED; KOTHARI, Himanshu M.; DAVE, Mayank Ghanshyambhai; PANDEY, Bipin
Patent: WO2011/48607 A1, 2011 ;
Location in patent: Page/Page column 16 ;
反应条件
1: (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline; 1,1'-carbonyldiimidazole in toluene T=20°C; 2.75 h; 2: (3R)-3-hydroxy-1-azabicyclo[2.2.2]octane With sodium hydride in N,N-dimethyl-formamide; toluene T=20 - 85°C;
参考文献
Koltai, Tamas; Nidam, Tamar; Gilboa, Eyal; Perlman, Nurit; Pinhasov, Michael; Abramov, Mili
Patent: US2008/114028 A1, 2008 ;
Location in patent: Page/Page column 9 ;
反应条件
1: (3R)-3-hydroxy-1-azabicyclo[2.2.2]octane With sodium hydride in tetrahydrofuran 0.75 h; Reflux; 2: (S)-1-phenyl-3,4-dihydro-1H-isoquinoline-2-carbonyl chloride in tetrahydrofuran 1.5 h; Reflux;
参考文献
ZAKLADY FARMACEUTYCZNE POLPHARMA SA; SZRAMKA, Roman; DRYGAS, Jersy; SZULC, Marcin
Patent: WO2011/86003 A1, 2011 ;
Location in patent: Page/Page column 12-13 ;
反应条件
1: chloroformic acid ethyl ester; (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline With potassium carbonate in water; toluene T=10 - 25°C; 2 h; 2: sodium ethanolate; (3R)-3-hydroxy-1-azabicyclo[2.2.2]octane in N,N-dimethyl-formamide; toluene T=20°C; 8 h; 3: With hydrogenchloride; potassium carbonate more than 3 stages;
参考文献
Astellas Pharma Inc.
Patent: EP1726304 A1, 2006 ;
Location in patent: Page/Page column 6 ;
反应条件
1: 2-(1H-imidazole-2-ylcarbonyl)-(1S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline With titanium(IV) isopropylate in tetrahydrofuran T=20°C; 0.5 h; 2: (3R)-3-hydroxy-1-azabicyclo[2.2.2]octane With sodium hydride in tetrahydrofuran Reflux; Product distribution / selectivity;
参考文献
Corporacion Medichem, S.L.
Patent: US2010/29944 A1, 2010 ;
Location in patent: Page/Page column 6 ;
