(3R,4S)-4-[4-(苄氧基)苯基]-1-(4-氟苯基)-3-[3-(4-氟苯基)-3-氧代丙基]氮杂环丁烷-2-酮合成路线 （共 32 条）
反应条件
1.1: hydroxylamine hydrochloride / pyridine / 0 - 20 °C 2.1: titanium(IV) isopropylate; N-ethyl-N,N-diisopropylamine; titanium tetrachloride / dichloromethane / 0 °C 2.2: -15 °C 3.1: N,O-bis-(trimethylsilyl)-acetamide / toluene / 0.5 h / 60 °C 3.2: 8 h / 60 °C 3.3: 20 h / 20 °C 4.1: hydrogenchloride; formaldehyd / water; tetrahydrofuran / 6 h / 20 °C View Scheme
反应条件
1.1: titanium(IV) isopropylate; N-ethyl-N,N-diisopropylamine; titanium tetrachloride / dichloromethane / 0 °C 1.2: 3 h / -15 °C 2.1: N,O-bis-(trimethylsilyl)-acetamide / toluene / 0.5 h / 60 °C 2.2: 8 h / 60 °C 3.1: hydrogenchloride; formaldehyd / water; tetrahydrofuran / 4 h / 20 °C View Scheme
反应条件
1.1: N,O-bis-(trimethylsilyl)-acetamide / toluene / 0.5 h / 60 °C 1.2: 8 h / 60 °C 1.3: 20 h / 20 °C 2.1: hydrogenchloride; formaldehyd / water; tetrahydrofuran / 6 h / 20 °C View Scheme
反应条件
methanesulfonic acid; dimethylsulfide borane complex; (R)-tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c]-[1,3,2]oxazaborole in tetrahydrofuran; methyl tertiarybutylether; toluene T=-25 - -20°C; 2.5 - 3.5 h; Product distribution / selectivity;
参考文献
TEVA PHARMACEUTICAL INDUSTRIES LTD.; TEVA PHARMACEUTICALS USA, INC.
Patent: WO2007/30721 A2, 2007 ;
Location in patent: Page/Page column 23; 24; 27 ;
反应条件
dimethylsulfide borane complex in tetrahydrofuran T=22°C; 3 h;
参考文献
Rosenblum, Stuart B.; Huynh, Tram; Afonso, Adriano; Davis Jr., Harry R.; Yumibe, Nathan; Clader, John W.; Burnett, Duane A.
Journal of Medicinal Chemistry, 1998 , vol. 41, # 6 p. 973 - 980
反应条件
hydrogenchloride in tetrahydrofuran
参考文献
Schering Corporation
Patent: US5856473 A1, 1999 ;
反应条件
hydrogen; palladium 10 on activated carbon in ethanol P=3102.97 Torr; 16 h;
参考文献
Schering Corporation
Patent: US2005/96307 A1, 2005 ;
Location in patent: Page/Page column 24 ;
反应条件
1: 70 percent / CBS; BH3-Me2S / toluene; CH2Cl2 / 2 h / -20 °C 2: 79 percent / ammonium formate; HOAc / Pd-C / methanol / 3 h / 45 - 55 °C / pH 3 - 5 View Scheme
参考文献
Rosenblum, Stuart B.; Huynh, Tram; Afonso, Adriano; Davis Jr., Harry R.; Yumibe, Nathan; Clader, John W.; Burnett, Duane A.
Journal of Medicinal Chemistry, 1998 , vol. 41, # 6 p. 973 - 980
反应条件
1: BH3*Me2S / tetrahydrofuran / 3 h / 22 °C 2: H2 / 10percent Pd/C / ethanol / 16 h / 3102.9 Torr 3: 0.260 g / pyridine / CH2Cl2 / 1 h / 22 °C View Scheme
参考文献
Rosenblum, Stuart B.; Huynh, Tram; Afonso, Adriano; Davis Jr., Harry R.; Yumibe, Nathan; Clader, John W.; Burnett, Duane A.
Journal of Medicinal Chemistry, 1998 , vol. 41, # 6 p. 973 - 980
反应条件
hydrogen; palladium on activated charcoal in ethanol P=3102.9 Torr; 12 h;
参考文献
IND-SWIFT LABORATORIES LIMITED
Patent: WO2008/96372 A2, 2008 ;
Location in patent: Page/Page column 21-22 ;
