(3S,4R)-3-氟-4-羟基哌啶-1-羧酸叔丁酯合成路线 （共 6 条）
反应条件
Me4NBH4 in methanol
T=0°C; 4.25 h; Inert atmosphere; enantioselective reaction;
参考文献
Shaw, Simon J.; Goff, Dane A.; Boralsky, Luke A.; Irving, Mark; Singh, Rajinder
Journal of Organic Chemistry, 2013 , vol. 78, # 17 p. 8892 - 8897
反应条件
1: sodium tetrahydroborate / methanol / 0 - 20 °C
2: Chiralpak AD-H column / ethanol; carbon dioxide / Resolution of racemate
View Scheme
参考文献
PFIZER INC.; GUIMARAES, Cristiano Ruch Werneck; MASCITTI, Vincent; MCCLURE, Kim Francis; MUNCHHOF, Michael John; ROBINSON, Ralph Pelton, Jr.
Patent: WO2011/36576 A1, 2011 ;
WO 2011/036576 A1
反应条件
1: 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo-[2.2.2]octane bis(tetrafluoroborate) / acetonitrile / 1.5 h / 20 °C
2: sodium tetrahydroborate / methanol / 0 - 20 °C
3: Chiralpak AD-H column / ethanol; carbon dioxide / Resolution of racemate
View Scheme
参考文献
PFIZER INC.; GUIMARAES, Cristiano Ruch Werneck; MASCITTI, Vincent; MCCLURE, Kim Francis; MUNCHHOF, Michael John; ROBINSON, Ralph Pelton, Jr.
Patent: WO2011/36576 A1, 2011 ;
WO 2011/036576 A1
反应条件
1: triethylamine / N,N-dimethyl-formamide / 20 - 80 °C
2: 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo-[2.2.2]octane bis(tetrafluoroborate) / acetonitrile / 1.5 h / 20 °C
3: sodium tetrahydroborate / methanol / 0 - 20 °C
4: Chiralpak AD-H column / ethanol; carbon dioxide / Resolution of racemate
View Scheme
参考文献
PFIZER INC.; GUIMARAES, Cristiano Ruch Werneck; MASCITTI, Vincent; MCCLURE, Kim Francis; MUNCHHOF, Michael John; ROBINSON, Ralph Pelton, Jr.
Patent: WO2011/36576 A1, 2011 ;
WO 2011/036576 A1
反应条件
1.1: L-Selectridereg; / tetrahydrofuran / 2 h / -35 - 0 °C
1.2: 0.25 h / 0 °C
1.3: 0 °C / pH 7 / Aqueous phosphate buffer
2.1: Chiralpak AD-H column / ethanol; carbon dioxide / Resolution of racemate
View Scheme
参考文献
PFIZER INC.; MASCITTI, Vincent; MCCLURE, Kim Francis; MUNCHHOF, Michael John; ROBINSON, Ralph Pelton
Patent: WO2011/61679 A1, 2011 ;
WO 2011/061679 A1
反应条件
1: sodium carbonate; N-fluoro-N-(phenylsulfonyl)benzene-sulfonamide; (R)-α-methylbenzylamine monotrichloroacetic acid / tetrahydrofuran / 24 h / -20 - -10 °C / |Inert atmosphere
2: Me4NBH4 / methanol / 4.25 h / 0 °C / |Inert atmosphere
View Scheme
参考文献
Shaw, Simon J.; Goff, Dane A.; Boralsky, Luke A.; Irving, Mark; Singh, Rajinder
Journal of Organic Chemistry, 2013 , vol. 78, # 17 p. 8892 - 8897
