- Preparation method of 3-aminopropanol or 3-aminopropionic acid derivative
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The invention provides a preparation method of an optically active 3-aminopropanol or 3-aminopropionic acid derivative, and belongs to the technical field of organic synthesis. A compound having a structure as shown in a formula II and a formula III is used as a raw material, and the optically active 3-aminopropanol or 3-aminopropionic acid derivative is obtained through four basic steps, namely dehydration condensation, hydrogenation reduction, reduction and hydrolysis. The raw materials adopted in the preparation method are easy to obtain and low in cost; as a chiral phosphine-transitional metal catalyst is used in the hydrogenation reduction reaction, the optically active 3-aminopropanol or 3-aminopropionic acid derivative is efficient, high in selectivity, low in cost and suitable forlarge-scale production. Compared with existing chemical resolution and chiral introduction, the asymmetric hydrogenation synthesis method provided by the invention only produces one chiral product, ishigh in yield, and has relatively high advantages in economy and raw material utilization rate.
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Paragraph 0246; 0257; 0258; 0260
(2018/10/11)
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- Sequential ruthenium catalysis for olefin isomerization and oxidation: Application to the synthesis of unusual amino acids
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How can you use a ruthenium isomerization catalyst twice? A ruthenium-catalyzed sequence for the formal two-carbon scission of allyl groups to carboxylic acids has been developed. The reaction includes an initial isomerization step using commercially available ruthenium catalysts followed by in situ transformation of the complex to a metal-oxo species, which is capable of catalyzing subsequent oxidation reactions. The method enables enantioselective syntheses of challenging α-tri- and tetrasubstituted α-amino acids including an expedient total synthesis of the antiepileptic drug levetiracetam.
- Liniger, Marc,Liu, Yiyang,Stoltz, Brian M.
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p. 13944 - 13949
(2017/11/06)
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- Development of a commercial process for (S)-β-phenylalanine (1)
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The development of a commercial manufacturing route for (S)-β-phenylalanine 8, a key pharmaceutical building block, is described. The different approaches which were investigated, based on catalytic asymmetric hydrogenation of enamide intermediates and on biocatalysis using acylase and lipase hydrolyses, are compared. The lipase resolution route was chosen for scale-up, and the final two-step process, based on readily available raw materials, is shown to be robust at full manufacturing scale
- Grayson, J. Ian,Roos, Juergen,Osswald, Steffen
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p. 1201 - 1206
(2011/12/16)
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- Enantiopure β3-neopentylglycine: synthesis and resolution
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A procedure has been developed for the large scale synthesis of enantiopure β3-neopentylglycine and its Cbz-protected derivative. The synthetic route developed in our laboratory features Cbz-protection of the racemic β-amino acid followed by resolution with l-norephedrine and provides the enantiomerically pure Cbz-β-neopentylglycine in good yield and excellent enantiopurity. No toxic or dangerous chemicals are used, allowing the scale-up of this procedure without major safety concerns.
- ter Wiel, Matthijs K.J.,Arnold, Mirjam,Peter, Sandra,Troltsch, Ingo,Merget, Stefan,Glaser, Florian,Schwarm, Michael,Bhatti, Harjinder S.,Kuriakose, Biju,Pol, Suryakant S.,Balamurugan, Mohanasundaram,Joshi, Viral V.
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experimental part
p. 478 - 482
(2009/09/08)
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