专利号:US-8729308-B2 优先权日:2009-12-01 标 题:Process for the preparation of tapentadol and intermediates thereof 发明人:MOTTA GIUSEPPE; VERGANI DOMENICO; BERTOLINI GIORGIO 权利人:MOTTA GIUSEPPE; VERGANI DOMENICO; BERTOLINI GIORGIO; EUTICALS SPA 摘要:The present invention refers to a new process for the synthesis of tapentadol comprising the quantitative resolution of the racemic mixture (V) to obtain the stereoisomer of (S)-3-(dimethylamino)-2-methyl-1-(3-nitrophenyl)-propan-1-one (VII) according to the Scheme 2 below n nusing the (2R,3R)—O,O′-dibenzoyltartaric chiral acid wherein said resolution is quantitative.n n The present invention also refers to some intermediate compounds of the new synthesis process of tapentadol.
专利号:US-2004110957-A1 优先权日:2002-12-05 标 题 :Process for the synthesis of an antiviral compound 发明人:WILKEN JOERG; NERENZ FRANK; KANSCHIK-CONRADSEN ANDREAS 权利人:HONEYWELL INT INC 摘要:In a process comprising synthesizing pyranes including [R—(R*,R*)]-N-[3-[1-[5,6-dihydro-4-hydroxy-2-oxo-6-(2-phenylethyl)-6-propyl-2H-pyran-3-yl]propyl]phenyl]-5-(trifluoromethyl)-2-pyridinesulfonamide the present invention comprises the improvements comprising: (a) providing a racemic mixture of 3-hydroxy-3-(2-phenylethyl)-hexanoate ethyl acetate by reacting said 1-phenyl-hexan-3-one with ethylbromoacetate under Reformatsky conditions; and (b) separating (R)-3-hydroxy-3-(2-phenylethyl)-hexanoic acid in enantiomeric excess by saponification and reverse resolution of the racemate of step (a) to produce a resolved product. In addition, the present invention comprises a reverse resolution process for separating an enantiomer from a mixture of enantiomers.
专利号:US-2006287397-A1 优先权日:2002-04-26 标 题:Dl-hydroxy-alkyl-phenylamides having anticonvulsive activity 发明人:MEZA TOLEDO SERGIO E 权利人:MEZA TOLEDO SERGIO E 摘要:New anticonvulsant compounds were synthesized and they include the compounds: DL-2-hydroxy-2-(3′,5′-bistrifluoromethylphenyl)butyramide, DL-2-hydroxy-2-(4′-trifluoromethylphenyl)butyramide, DL-2-hydroxy-2-(3′,4′-dichlorophenyl)butyramide, DL-2-hydroxy-2-(3′-bromophenyl)butyramide, DL-2-hydroxy-2-(4′-bromophenyl)butyramide, DL-2-hydroxy-2-(3′-nitrophenyl)butyramide, DL-3-hydroxy-3-(3′,4′-dichlorophenyl)pentanamide, DL-3-hydroxy-3-(4′-bromophenyl)pentanamide, DL-4-hydroxy-4-(3′,4′-dichlorophenyl) hexanamide and DL-4-hydroxy-4-(4′-bromophenyl)hexanamide. They have a significant anticonvulsant activity against pentylenetetrazol-induced seizures as well as unexpected differences in anticonvulsant activity respect those of the non-halogenated compounds. The invention further provides methods for the synthesis of the DL-hydroxy-alkyl-phenyl amides as exemplified in the examples.
[参考文献]: P Udhayakala, Et Al. Vibrational Spectroscopy Investigation Using Ab Initio And Density Functional Theory On 3'-Chloropropiophenone And 3'-Nitropropiophenone. Spectrochim Acta A Mol Biomol Spectrosc. 2010 Feb;75(2):567-73.
合成参考文献
摘要:Cunha, J. C.; Dedeiras, B.; Negrão, A. C. R.; Marques, M. M. B., Science of Synthesis: Hypervalent Halogens in Organic Synthesis, (2025) .