(3S,4r)-1-boc-3-羟基甲基-4-(4-氟苯基)-哌啶合成路线 （共 32 条）
反应条件
1: Cs2CO3 / o-xylene / 20 h / 130 °C 2: 99 mg / TFA / CH2Cl2 / 0.25 h View Scheme
参考文献
Amat, Mercedes; Bosch, Joan; Hidalgo, Jose; Canto, Margalida; Perez, Maria; Llor, Nuria; Molins, Elies; Miravitlles, Carles; Orozco, Modesto; Luque, Javier
Journal of Organic Chemistry, 2000 , vol. 65, # 10 p. 3074 - 3084
反应条件
1: triethylamine / toluene / 2 h / 23 °C 2: 86 percent / sodium methoxide / toluene; methanol / 14 h / 80 - 110 °C 3: 99 percent / HCl / propan-2-ol / 5 h / 75 °C View Scheme
参考文献
Journal of the American Chemical Society, , vol. 125, # 37 p. 11204 - 11205
反应条件
triethylamine in dichloromethane
T=20°C; 20 h;
参考文献
XENON PHARMACEUTICALS INC.; SUN, Shaoyi; ZENOVA, Alla, Yurevna; CHAFEEV, Mikhail; JIA, Qi; ZHANG, Zaihui; OBALLA, Renata, Marcella
Patent: WO2013/64983 A1, 2013 ;
Location in patent: Page/Page column 80 ;
WO 2013/064983 A1
反应条件
1: With dimethylsulfide borane complex in tetrahydrofuran
T=0 - 20°C;
2: With methanol in tetrahydrofuran
T=0°C;
参考文献
Grundschober, Christophe; Schnider, Patrick
Patent: US2007/232652 A1, 2007 ;
Location in patent: Page/Page column 15 ;
US 20070232652 A1
反应条件
hydrogen; 20percent Pd(OH)2-C in ethyl acetate
T=25°C; Hydrogenolysis; Boc-protection; 15 h;
参考文献
Amat, Mercedes; Bosch, Joan; Hidalgo, Jose; Canto, Margalida; Perez, Maria; Llor, Nuria; Molins, Elies; Miravitlles, Carles; Orozco, Modesto; Luque, Javier
Journal of Organic Chemistry, 2000 , vol. 65, # 10 p. 3074 - 3084
反应条件
hydrogen; palladium 10 on activated carbon in 1,4-dioxane
17 h;
参考文献
CONCERT PHARMACEUTICALS INC.
Patent: WO2007/16431 A2, 2007 ;
Location in patent: Page/Page column 55 ;
WO 2007/016431 A2
反应条件
1: 77 percent / Et3N / tetrahydrofuran / 4 h / Heating
2: Na2CO3 / CH2Cl2 / 0.5 h
3: 8.36 g / EtONa / ethanol / 0.5 h / Heating
4: 89 percent / CuCl2; t-BuONa; (R)-p-tolBINAP / PMHS; tert-amyl alcohol / fluorobenzene / 0.75 h
5: 79 percent / MeOH; NaH / toluene / 4 h / Heating
6: 98 percent / BH3 / tetrahydrofuran / 18 h / Heating
7: CAN / acetonitrile; H2O / 0.5 h / 20 °C
8: 268 mg / NaOH / toluene; H2O / 3 h / 20 °C
View Scheme
参考文献
Hughes, Gregory; Kimura, Masanari; Buchwald, Stephen L.
Journal of the American Chemical Society, 2003 , vol. 125, # 37 p. 11253 - 11258
反应条件
1: Na2CO3 / CH2Cl2 / 0.5 h
2: 8.36 g / EtONa / ethanol / 0.5 h / Heating
3: 89 percent / CuCl2; t-BuONa; (R)-p-tolBINAP / PMHS; tert-amyl alcohol / fluorobenzene / 0.75 h
4: 79 percent / MeOH; NaH / toluene / 4 h / Heating
5: 98 percent / BH3 / tetrahydrofuran / 18 h / Heating
6: CAN / acetonitrile; H2O / 0.5 h / 20 °C
7: 268 mg / NaOH / toluene; H2O / 3 h / 20 °C
View Scheme
参考文献
Hughes, Gregory; Kimura, Masanari; Buchwald, Stephen L.
Journal of the American Chemical Society, 2003 , vol. 125, # 37 p. 11253 - 11258
反应条件
1: 89 percent / CuCl2; t-BuONa; (R)-p-tolBINAP / PMHS; tert-amyl alcohol / fluorobenzene / 0.75 h
2: 79 percent / MeOH; NaH / toluene / 4 h / Heating
3: 98 percent / BH3 / tetrahydrofuran / 18 h / Heating
4: CAN / acetonitrile; H2O / 0.5 h / 20 °C
5: 268 mg / NaOH / toluene; H2O / 3 h / 20 °C
View Scheme
参考文献
Hughes, Gregory; Kimura, Masanari; Buchwald, Stephen L.
Journal of the American Chemical Society, 2003 , vol. 125, # 37 p. 11253 - 11258
反应条件
1: 8.36 g / EtONa / ethanol / 0.5 h / Heating
2: 89 percent / CuCl2; t-BuONa; (R)-p-tolBINAP / PMHS; tert-amyl alcohol / fluorobenzene / 0.75 h
3: 79 percent / MeOH; NaH / toluene / 4 h / Heating
4: 98 percent / BH3 / tetrahydrofuran / 18 h / Heating
5: CAN / acetonitrile; H2O / 0.5 h / 20 °C
6: 268 mg / NaOH / toluene; H2O / 3 h / 20 °C
View Scheme
参考文献
Hughes, Gregory; Kimura, Masanari; Buchwald, Stephen L.
Journal of the American Chemical Society, 2003 , vol. 125, # 37 p. 11253 - 11258
