外消旋alpha-羟基布洛芬合成路线 （共 19 条）
反应条件
lithium aluminium tetrahydride; titanium tetrachloride in tetrahydrofuran
T=-5°C; 0.5 h;
参考文献
Garcia, Mariano; Del Campo, Carmen; Sinisterra, Jose V.; Llama, Emilio F.
Tetrahedron Letters, 1993 , vol. 34, # 49 p. 7973 - 7974
反应条件
1.1: magnesium / tetrahydrofuran
1.2: 83 percent / tetrahydrofuran / -78 - 25 °C
2.1: 91 percent / KOH / methanol / 2 h / 20 °C
View Scheme
参考文献
Bellezza, Francesca; Cipiciani, Antonio; Ricci, Giacomo; Ruzziconi, Renzo
Tetrahedron, 2005 , vol. 61, # 33 p. 8005 - 8012
反应条件
water; potassium carbonate in ethanol
4 h; Heating; Yield given;
参考文献
Kuchar; Brunova; Rejholec; et al.
Collection of Czechoslovak Chemical Communications, 1984 , vol. 49, # 1 p. 122 - 136
反应条件
1: 79.4 percent / AlCl3 / 1,2-dichloro-ethane / 1) addition of AlCl3 at temperature not exceeding 15 deg C 2) 10 deg C, 1 h 3) 20 deg C, 4 h
2: Mg / 1) ether, 0 deg C, 4 h 2) 20 deg C, 3 h
3: K2CO3, H2O / aq. ethanol / 4 h / Heating
View Scheme
参考文献
Kuchar; Brunova; Rejholec; et al.
Collection of Czechoslovak Chemical Communications, 1984 , vol. 49, # 1 p. 122 - 136
反应条件
1: Mg / 1) ether, 0 deg C, 4 h 2) 20 deg C, 3 h
2: K2CO3, H2O / aq. ethanol / 4 h / Heating
View Scheme
参考文献
Kuchar; Brunova; Rejholec; et al.
Collection of Czechoslovak Chemical Communications, 1984 , vol. 49, # 1 p. 122 - 136
反应条件
1: caesium carbonate; triethyl phosphite; oxygen / dimethyl sulfoxide / 24 h / 25 °C / 760.05 Torr / |Schlenk technique
2: ethanol; potassium hydroxide / 4 h / 20 °C
View Scheme
参考文献
Liang, Yu-Feng; Jiao, Ning
Angewandte Chemie - International Edition, 2014 , vol. 53, # 2 p. 548 - 552
Angew. Chem., 2014 , vol. 53, # 2 p. 558 - 562,5
反应条件
1.1: 4-(N,N-dimethlyamino)pyridine / dichloromethane / 0.08 h / 0 °C
1.2: 3.08 h / 0 - 20 °C
2.1: caesium carbonate; triethyl phosphite; oxygen / dimethyl sulfoxide / 24 h / 25 °C / 760.05 Torr / |Schlenk technique
3.1: ethanol; potassium hydroxide / 4 h / 20 °C
View Scheme
参考文献
Liang, Yu-Feng; Jiao, Ning
Angewandte Chemie - International Edition, 2014 , vol. 53, # 2 p. 548 - 552
Angew. Chem., 2014 , vol. 53, # 2 p. 558 - 562,5
反应条件
1: NADPH; cytochrome P450 3A4 / 20 h / 37 °C / aq. phosphate buffer; Enzymatic reaction
2: porcine liver esterase / Enzymatic reaction
View Scheme
参考文献
Xie, Gang; Wong, Chi C; Cheng, Ka-Wing; Huang, Liqun; Constantinides, Panayiotis P.; Rigas, Basil
British Journal of Pharmacology, 2012 , vol. 167, # 1 p. 222 - 232
参考文献
SANOFI and Industria Chimica Prodotti FRANCIS S.p.A.
Patent: US4713485 A1, 1987 ;
