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Resolution of 1,1’-Bi-2-Naphthols with Synthesized Derivant of L-Glutamic Acid

Author: ChenZongHua
Tutor: LiuBo
School: Harbin University of Science and Technology
Course: Applied Chemistry
Keywords: 1,1 ' - Bi-2 - naphthol ( BINOL ) Pyrrolidone derivatives Enantiomers were Chiral Synthesis
CLC: O621.2
Type: Master's thesis
Year: 2007
Downloads: 155
Quote: 0
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Abstract


1,1 '- bi-2 - naphthol (BINOL) is a C2- axis of a typical chiral molecules, and is widely used as a chiral ligand , involved in the catalytic asymmetric synthesis reaction . The synthesis of enantiomerically pure (R)-BINOL (S)-BINOL has been extensively studied , there are two kinds of preparation methods , i.e. by resolving the racemic BINOL and asymmetric catalytic oxidative coupling . Synthesis of L-glutamic acid derivative ( S ) -2 - pyrrolidone-5 - carboxanilide split racemic BINOL is the main topic of this thesis . This work mainly includes the following aspects : 1 , (S) -2 - pyrrolidone-5 - carboxanilide high performance liquid chromatography (HPLC) enantiomeric excess (ee) value detection methods . 1) the network polymer of L-tartaric acid - type chiral stationary phase , 2 - pyrrolidone-5 - carboxanilide HPLC enantiomeric separation method examines the stationary phase monomer type , mobile phase composition and flow rate and so the impact on the separation of enantiomers . 2) and the optimized chromatographic conditions : KR-100-TBB (250mm × 4.6mm, 5um) column, mobile phase n-hexane and isopropanol (90:10, v / v), flow rate was 1.0mL / min, room temperature . 3) in the optimal chromatographic conditions ( R ) type and (S)- enantiomer retention time of 19.2min and 21.5min , the separation degree of 1.51. 2 , Study of ( S ) -2 - pyrrolidone-5 - carboxymethyl anilide synthesis method. 1) respectively to the L-glutamic acid , L - pyroglutamic acid , and L- pyroglutamic acid methyl ester 4 as raw materials , the synthesis of the optically pure ( S ) -2 - pyrrolidone-5 - carboxanilide . 2) Study of the ( S ) -2 - pyrrolidone-5 - carboxanilide synthesis process product racemization, discusses the influence of the reaction time , temperature, etc. . 3 ) describes the product racemization mechanism and the sub - product, 2 - the alkenyl aniline pyrrolidine-5 - carboxanilide mechanism of formation . 3, improved the racemic 1,1 '- bi-2 - naphthol 6 using ( S ) -2 - pyrrolidone-5 - carboxanilide split . 1) controlled by kinetics crystallization method , improvement of the ( S ) -2 - pyrrolidone-5 - carboxanilide split racemic the BINOL the process , obtained ee values ??are greater than 99% of the (R)-BINOL ( S)-BINOL. 2 ) orthogonal experiment method to study the reaction time , split dosage , solvent composition , as well as the volume of solvent in the yield of (R)-BINOL and (S)-BINOL split process .

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