(S)-(+)-布洛芬合成路线 （共 120 条）
反应条件
1: With sodium chlorite; 1,1,2,2-tetramethylethylene in diethyl ether T=0 - 20°C; Inert atmosphere; 2: With sulfuric acid in diethyl ether 0.166667 h; Inert atmosphere; optical yield given as percent ee;
参考文献
Smith, Craig R.; Babu, T.V. Rajan
Journal of Organic Chemistry, 2009 , vol. 74, # 8 p. 3066 - 3072
反应条件
1: With (S)-(3-OH-4,4-di-Me-2-oxopyrrolidin-1-yl)CH2COOH on resin; triethylamine in tetrahydrofuran T=0°C; 2: With lithium hydroxide in tetrahydrofuran; water T=20°C; 4 h; Further stages. Title compound not separated from byproducts.;
参考文献
Akkari; Calmes; Mai; Rolland; Martinez
Journal of Organic Chemistry, 2001 , vol. 66, # 17 p. 5859 - 5865
反应条件
1: 90 percent / ICl / CH2Cl2 / 0.5 h / Ambient temperature 2: 75 percent / RuCl3*H2O, NaIO4 / CCl4; acetonitrile; H2O / 1.25 h / Ambient temperature 3: 1.) ZnCl2, 2.) dichlorobis(triphenylphosphine)palladium(II), DIBALH / 1.) THF, RT, 10 min, 2.) THF, RT, 1.5 h 4: 69 percent / H2 / 10percent Pd/C / ethyl acetate / 1.5 h / Ambient temperature View Scheme
参考文献
Hamon, David P.G.; Massy-Westropp, Ralph A.; Newton, Josephine L.
Tetrahedron, 1995 , vol. 51, # 46 p. 12645 - 12660
反应条件
1: 1.) H2, 1M NaOH / 1.) 10percent Pd/C / 1.) EtOH, 1.5 h, 2.) EtOH, -60 deg C, 5 h 2: 90 percent / ICl / CH2Cl2 / 0.5 h / Ambient temperature 3: 75 percent / RuCl3*H2O, NaIO4 / CCl4; acetonitrile; H2O / 1.25 h / Ambient temperature 4: 1.) ZnCl2, 2.) dichlorobis(triphenylphosphine)palladium(II), DIBALH / 1.) THF, RT, 10 min, 2.) THF, RT, 1.5 h 5: 69 percent / H2 / 10percent Pd/C / ethyl acetate / 1.5 h / Ambient temperature View Scheme
参考文献
Hamon, David P.G.; Massy-Westropp, Ralph A.; Newton, Josephine L.
Tetrahedron, 1995 , vol. 51, # 46 p. 12645 - 12660
反应条件
1: 75 percent / RuCl3*H2O, NaIO4 / CCl4; acetonitrile; H2O / 1.25 h / Ambient temperature 2: 1.) ZnCl2, 2.) dichlorobis(triphenylphosphine)palladium(II), DIBALH / 1.) THF, RT, 10 min, 2.) THF, RT, 1.5 h 3: 69 percent / H2 / 10percent Pd/C / ethyl acetate / 1.5 h / Ambient temperature View Scheme
参考文献
Hamon, David P.G.; Massy-Westropp, Ralph A.; Newton, Josephine L.
Tetrahedron, 1995 , vol. 51, # 46 p. 12645 - 12660
反应条件
lithium hydroxide; dihydrogen peroxide in dichloromethane
参考文献
Benoit, David; Coulbeck, Elliot; Eames, Jason; Motevalli, Majid
Tetrahedron Asymmetry, 2008 , vol. 19, # 9 p. 1068 - 1077
反应条件
in ethanol; water T=0°C; 4 h; Inert atmosphere;
参考文献
Bhattacharya, Apurba; Murphy, David
Organic Process Research and Development, 2003 , vol. 7, # 5 p. 717 - 722
反应条件
1: 3,3'-All2-2,2'-O2P-N[(S)-CH(Ph)Et]2-1,1'-Ph2 / copper thiophenecarboxylate / diethyl ether; toluene / 16 h / -35 °C 2: 80 percent / NaNO2; AcOH / dimethylsulfoxide / 24 h / 35 °C View Scheme
参考文献
Polet, Damien; Alexakis, Alexandre
Tetrahedron Letters, 2005 , vol. 46, # 9 p. 1529 - 1532
反应条件
1: hydrogen / Pearlman's catalyst / ethanol / 6 h 2: CrO3; H2SO4 / acetone; H2O / 2 h / 20 °C View Scheme
参考文献
Ishibashi, Hiroyuki; Maeki, Momoe; Yagi, Junko; Ohba, Masashi; Kanai, Tae
Tetrahedron, 1999 , vol. 55, # 19 p. 6075 - 6080
反应条件
(S)-HBTM; N-ethyl-N,N-diisopropylamine in toluene T=0°C; 24 h; optical yield given as percent eeenantioselective reaction;
参考文献
Yang, Xing; Birman, Vladimir B.
Advanced Synthesis and Catalysis, 2009 , vol. 351, # 14-15 p. 2301 - 2304
