(S)-(+)-布洛芬合成路线 （共 120 条）
反应条件
(-)-(S)-β-Np-BTM; trimethylacetic anhydride; N-ethyl-N,N-diisopropylamine in dichloromethane T=20°C; 12 h; Inert atmosphereResolution of racemate; optical yield given as percent eeenantioselective reaction;
参考文献
Shiina, Isamu; Nakata, Kenya; Ono, Keisuke; Onda, Yu-Suke; Itagaki, Makoto
Journal of the American Chemical Society, 2010 , vol. 132, # 33 p. 11629 - 11641
反应条件
1.1: QT / toluene / 24 h / 20 °C 2.1: sodium hypophosphite monohydrate / tetrahydrofuran; methanol / 1 h / 20 °C / pH 5.2 / aq. acetate buffer 3.1: lithium hydroxide hydrate / tetrahydrofuran; water / 3 h / 20 °C 3.2: pH 4 View Scheme
参考文献
Rana, Nirmal K.; Singh, Vinod K.
Organic Letters, 2011 , vol. 13, # 24 p. 6520 - 6523
反应条件
1.1: lithium hydroxide hydrate / tetrahydrofuran; water / 72 h / 20 °C 1.2: pH 1 2.1: 4-(N,N-dimethlyamino)pyridine; diisopropyl-carbodiimide / dichloromethane / 12 h / 20 °C 3.1: QT / toluene / 24 h / 20 °C 4.1: sodium hypophosphite monohydrate / tetrahydrofuran; methanol / 1 h / 20 °C / pH 5.2 / aq. acetate buffer 5.1: lithium hydroxide hydrate / tetrahydrofuran; water / 3 h / 20 °C 5.2: pH 4 View Scheme
参考文献
Rana, Nirmal K.; Singh, Vinod K.
Organic Letters, 2011 , vol. 13, # 24 p. 6520 - 6523
反应条件
1.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / -78 - 20 °C / Inert atmosphere 1.2: 12 h / -78 - 20 °C 2.1: lithium hydroxide hydrate / tetrahydrofuran; water / 72 h / 20 °C 2.2: pH 1 3.1: 4-(N,N-dimethlyamino)pyridine; diisopropyl-carbodiimide / dichloromethane / 12 h / 20 °C 4.1: QT / toluene / 24 h / 20 °C 5.1: sodium hypophosphite monohydrate / tetrahydrofuran; methanol / 1 h / 20 °C / pH 5.2 / aq. acetate buffer 6.1: lithium hydroxide hydrate / tetrahydrofuran; water / 3 h / 20 °C 6.2: pH 4 View Scheme
参考文献
Rana, Nirmal K.; Singh, Vinod K.
Organic Letters, 2011 , vol. 13, # 24 p. 6520 - 6523
反应条件
Lipase MY in 2,2,4-trimethylpentane T=37°C; 100 h; Title compound not separated from byproducts;
参考文献
Chang, Chun-Sheng; Tsai, Shau-Wei; Lin, Chun-Nan
Tetrahedron Asymmetry, 1998 , vol. 9, # 16 p. 2799 - 2807
反应条件
1.1: triphenylmethylpotassium / 1,2-dimethoxy-ethane; various solvent(s) / 0.25 h / -78 °C 1.2: 1,2-dimethoxy-ethane; various solvent(s) / -78 °C 2.1: methanol / Heating 3.1: Acid hydrolysis View Scheme
参考文献
Sarakinos, Georgios; Corey
Organic Letters, 1999 , vol. 1, # 11 p. 1741 - 1744
反应条件
1.1: 90 percent / 4-(dimethylamino)pyridine; 1,3-dicyclohexylcarbodiimide; 4 Angstroem molecular sieves / CH2Cl2 / 4 h / 23 °C 2.1: triphenylmethylpotassium / 1,2-dimethoxy-ethane; various solvent(s) / 0.25 h / -78 °C 2.2: 1,2-dimethoxy-ethane; various solvent(s) / -78 °C 3.1: methanol / Heating 4.1: Acid hydrolysis View Scheme
参考文献
Sarakinos, Georgios; Corey
Organic Letters, 1999 , vol. 1, # 11 p. 1741 - 1744
反应条件
1.1: sodium hypophosphite monohydrate / tetrahydrofuran; methanol / 1 h / 20 °C / pH 5.2 / aq. acetate buffer 2.1: lithium hydroxide hydrate / tetrahydrofuran; water / 3 h / 20 °C 2.2: pH 4 View Scheme
参考文献
Rana, Nirmal K.; Singh, Vinod K.
Organic Letters, 2011 , vol. 13, # 24 p. 6520 - 6523
反应条件
hydrogenchloride; (S)-BNPPA; oxygen; copper dichloride; palladium dichloride in tetrahydrofuran P=760 Torr; 18 h; Ambient temperatureor (R)-BNPPA, var. educt/BNPPA/PdCl2 ratios; other olefine; Product distribution;
参考文献
Alper, Howard; Hamel, Nathalie
Journal of the American Chemical Society, 1990 , vol. 112, # 7 p. 2803 - 2804
反应条件
1: 90 percent / POCl3, Py / CH2Cl2 / 0 - 25 °C 2: K3Fe(CN)6, K2CO3, OsO4, (DHQD)2-PHAL, MeSO2NH2 / H2O; 2-methyl-propan-2-ol; toluene / 28 h / 0 °C 3: HCOONH4 / Pd-C / ethanol / 6 h / Heating 4: Jone's reagent / acetone / 8 h / 0 °C View Scheme
参考文献
Nandanan; Jayachandran; Phukan, Prodeep; Pais, Godwin C. G.; Sudalai
Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1998 , vol. 37, # 12 p. 1221 - 1227
