79559-97-0Relevant academic research and scientific papers
Catalytic Lewis and Br?nsted acid syn-diastereoselective benzylic substitutions of α-hydroxy-β-nitro- and α-hydroxy-β-azido-alkyl arenes
Chénard, étienne,Cusson, Jean-Philippe,Hanessian, Stephen,Hensienne, Rapha?l
, p. 292 - 306 (2020/06/17)
A series of alkyl and alkenyl p-methoxy arenes containing α,β-disubstituted diamino and amino alcohol groups were synthesized from β-nitro and β-azido benzylic alcohols in the presence of AuCl3 as catalyst. The formation of predominantly syn-disubstituted products were rationalized on the basis of mechanistic considerations and transition state models relying on A1,3-allylic strain. The products could have utility in the design of medicinally relevant compounds and as chiral ligands for asymmetric catalysis. A new synthesis of (+)-sertraline (Zoloft) was achieved.
Preparation method of chiral sertraline hydrochloride
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Paragraph 0039; 0042-0044; 0047-0049; 0052-0054; 0057-0059, (2020/10/21)
The invention relates to a preparation method of chiral sertraline hydrochloride, which comprises: 1) carrying out a reaction on cis-sertraline hydrochloride and an inorganic alkali in a toluene and water mixed solution, carrying out oil layer concentration to remove a solvent, adding an alcohol and water mixed solvent to dissolve the residue, and adding L-glutamic acid to carry out resolution toobtain a crude product sertraline glutamate; 2) recrystallizing the crude sertraline glutamate to obtain refined sertraline glutamate; and 3) reacting the refined glutamic acid sertraline with inorganic alkali in a mixed solution of water and toluene, concentrating an oil layer to remove the solvent, adding ethanol into residues for dissolving, and then adding a hydrogen chloride ethanol solutionfor crystallization to obtain the cis-(1S, 4S)-sertraline hydrochloride. The method is high in yield; the cis-(1S, 4S)-sertraline hydrochloride is high in purity, low in cost and suitable for industrial production.
Concise enantioselective synthesis of (+)-sertraline and (-)-CP-52002 using proline catalysis
Kalshetti, Rupali,Venkataramasubramanian,Kamble, Sanjay,Sudalai, Arumugam
supporting information, p. 1053 - 1055 (2016/02/16)
A short enantioselective synthesis of (+)-sertraline and its C4 epimer (-)-CP-52002 with an overall yield of 30%, respectively, as its hydrochloride has been described. The key steps are the proline catalyzed Mannich reaction of acetaldehyde and acid catalyzed intramolecular Friedel-Crafts' alkylation reaction of olefin proceeding with high optical purities.
Asymmetric hydrogenation of N-alkyl and N-aryl ketimines using chiral cationic Ru(diamine) complexes as catalysts: The counteranion and solvent effects, and substrate scope
Chen, Fei,Ding, Ziyuan,He, Yanmei,Qin, Jie,Wang, Tianli,Fan, Qing-Hua
, p. 5248 - 5257 (2012/08/08)
Asymmetric hydrogenation of N-alkyl and N-aryl ketimines catalyzed by chiral cationic η6-arene-(N-monosulfonylated diamine) Ru(II) complexes has been investigated. Strong counteranion and solvent effects on the enantioselectivity were observed. The ruthenium catalyst bearing non-coordinating BArF- anion was found to be particularly effective for the hydrogenation of acyclic and exocyclic N-alkyl ketimines in the presence of (Boc)2O in dichloromethane or even under solvent-free conditions, providing chiral amines with up to >99% ee and full conversions. Alternatively, the ruthenium catalyst bearing achiral phosphate anion together with corresponding phosphoric acid as the additive was also efficient for the hydrogenation of N-alkyl ketimines in the absence of (Boc)2O with excellent enantioselectivities and full conversions. For N-aryl ketimines lower enantiomeric excesses were observed by using the ruthenium catalyst bearing BArF- anion. This catalytic protocol thus provides a facile and practical access to optically active amines and has been successfully employed in the gram-scale synthesis of enantiomerically pure (+)-sertraline.
Stereoselective amination of chiral benzylic ethers using chlorosulfonyl isocyanate: Total synthesis of (+)-Sertraline
Lee, Sang Hwi,Kim, In Su,Li, Qing Ri,Dong, Guang Ri,Jeong, Lak Shin,Jung, Young Hoon
, p. 10011 - 10019 (2012/02/05)
The stereoselective amination of various chiral benzylic ethers using chlorosulfonyl isocyanate is developed, and the application of this method to the total synthesis of a potent antidepressant, (+)-sertraline, from readily available 1-naphthol is also described (Figure presented).
Asymmetric hydrogenation of N-Alkyl ketimines with phosphine-free, chiral, cationic Ru-MsDPEN catalysts
Chen, Fei,Wang, Tianli,He, Yanmei,Ding, Ziyuan,Li, Zhiwei,Xu, Lijin,Fan, Qing-Hua
, p. 1109 - 1113 (2011/03/21)
(Solvent) free and easy: A phosphine-free, chiral, cationic Ru-MsDPEN complex [(S,S)-1] is found to be an efficient catalyst for the enantioselective hydrogenation of a range of often-problematic N-alkyl ketimines (see scheme). This new method provides a more practical and greener synthetic approach to optically active amines, particularly N-alkyl amines, such as Sertraline.
AN IMPROVED PROCESS FOR THE MANUFACTURE OF SERTRALINE
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Example 2, (2010/08/04)
A process for preparing (±)-cis-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1- naphthalenamine (sertraline) and/or a pharmaceutically acceptable acid addition salt thereof comprising hydrogenation of 4-(3,4-dichlorophenyl)-3,4-dihydro-N-methyl-1- naphthalenimine (sertraline-1-imine) in the presence of a polar solvent using palladium / alumina as a catalyst at a temperature ranging from 25°C to 35°C to obtain (±)-cis/trans- sertraline with the (±)-cis racemate of sertraline as the major product.
Novel process for the preparation of sertraline hydrochloride form II
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Page/Page column 2-3, (2009/02/11)
The present invention relates to novel processes to produce sertraline hydrochloride Form II comprising the steps of forming a solution of sertraline hydrochloride in a polar organic solvent and adding this solution to a less polar organic solvent.
Sertraline acid addition salt, its preparation and its use in the preparation of sertraline hydrochloride form II
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Page/Page column 3, (2008/06/13)
The present invention relates to novel acid addition salts of sertraline, their preparation and their use in the preparation of crystalline Form-II of Sertraline hydrochloride.
AN IMPROVED PROCESS FOR THE PREPARATION OF SERTRALINE
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Page/Page column 4, (2008/06/13)
The present invention relates to a process for preparing sertraline of high purity by hydrogenating the corresponding imine compound (Schiff base) in the presence of amine salt and/or amide salt using a catalyst preferably a palladium or platinum catalyst.
