合成路线:Asymmetric reduction of ketone (III) with catecholborane or borane璵ethyl sulfide complex and CBS-oxazaborolidene as catalyst afforded [(R)-(+)-I] or [(S)-(?-I].
参考文献标题:Process for obtaining enantiomers of cizolirtine
文献作者:Frigola-Constansa,J.; Torrens-Jover,A.(Laboratorios del Dr.Esteve,SA)
参考来源:EP 1029852; ES 2130083; US 6118009; WO 9907684
合成路线:The transesterification of [(?-I] with vinyl acetate enzymatically catalyzed (lipase) allowed the selective recovery of the enatiomer [(R)-(+)-I] and the hydrolysis and racemization of the undesired enantiomer [(S)-(?-II] with hydrochloric acid.
参考文献标题:Method for separating carbinols
文献作者:Frigola Constansa,J.; Cuberes Altisent,M.R.; Berrocal Romero,J.M.; Gotor Santamaria,V.(Laboratorios del Dr.Esteve,SA)
参考来源:ES 2128959; FR 2742147; US 5849931; WO 9720817
合成路线:The optical resolution of (?-cizolirtine was accomplished by recrystallizing diastereoisomeric salts formed with the antipodes of di-p-toluoyltartaric acid in isopropanol.
参考文献标题:Resolution of amines
文献作者:Frigola-Constansa,J.; Torrens-Jover,A.(Laboratorios del Dr.Esteve,SA)
参考来源:EP 1024137; ES 2130079; US 6187930; WO 9902500
合成路线:The key compound 5-(alpha-hydroxybenzyl)-1-methyl-1H-pyrazole [(?-I] was obtained by two related ways: 1) by condensation of N-methylpyrazole with benzonitrile and butyl lithium in tetrahydrofuran and reduction of the obtained ketone with sodium borohydride in methanol or 2) by condensation of N-methylpyrazole with benzaldehyde and butyl lithium in THF/toluene.The alkylation of [(?-I] with 2-(dimethylamino)ethyl chloride hydrochloride was carried out using phase transfer conditions and reaction with citric acid using propanone as solvent.
合成路线:The optical resolution of (?-cizolirtine was accomplished by recrystallizing diastereoisomeric salts formed with the antipodes of di-p-toluoyltartaric acid in isopropanol.
合成路线:Resolution of alcohol [(?-I] as its diastereomeric O-acetylmandelate esters and saponification of each of them in ethanol in the presence of catalytic amounts of sodium cyanide yielded the enantiomerically pure alcohols [(R)-(+)-I] and [(S)-(?-I].
合成路线:The transesterification of [(?-I] with vinyl acetate enzymatically catalyzed (lipase) allowed the selective recovery of the enatiomer [(R)-(+)-I] and the hydrolysis and racemization of the undesired enantiomer [(S)-(?-II] with hydrochloric acid.
合成路线:Asymmetric reduction of ketone (III) with catecholborane or borane璵ethyl sulfide complex and CBS-oxazaborolidene as catalyst afforded [(R)-(+)-I] or [(S)-(?-I].
合成路线:Ethyl (R)-mandelate [(R)-IV] was protected as its tert-butyldimethylsilyl ether and reduced with DIBAL to [(R)-V],which was treated with ethoxycarbonylmethyl-enetriphenylphosphorane,followed by reduction to give [(R)-VI].Subsequent oxidation to [(R)-VII] and cyclization by reaction with methylhydrazine afforded a mixture of pyrazolines [(R)-VIII].Oxidation to pyrazole and deprotection yielded [(R)-(+)-I].
参考文献标题:Cizolirtine Citrate
文献作者:Farr? A.J.; Frigola,J.
参考来源:Drugs Fut 2002,27(8),721
合成路线:Resolution of alcohol [(?-I] as its diastereomeric O-acetylmandelate esters and saponification of each of them in ethanol in the presence of catalytic amounts of sodium cyanide yielded the enantiomerically pure alcohols [(R)-(+)-I] and [(S)-(?-I].
合成路线:Ethyl (R)-mandelate [(R)-IV] was protected as its tert-butyldimethylsilyl ether and reduced with DIBAL to [(R)-V],which was treated with ethoxycarbonylmethyl-enetriphenylphosphorane,followed by reduction to give [(R)-VI].Subsequent oxidation to [(R)-VII] and cyclization by reaction with methylhydrazine afforded a mixture of pyrazolines [(R)-VIII].Oxidation to pyrazole and deprotection yielded [(R)-(+)-I].
参考文献标题:Preparation of the enantiomers of the analgesic E-3710
文献作者:Hueso,J.; Frigola,J.; Farr? A.; Berrocal,J.; Gutierrez,B.
参考来源:Bioorg Med Chem Lett 1993,3(2),269
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