79617-96-2Relevant academic research and scientific papers
Chemoenzymatic Synthesis of Sertraline
Marx, Lisa,Ríos-Lombardía, Nicolás,Süss, Philipp,H?hne, Matthias,Morís, Francisco,González-Sabín, Javier,Berglund, Per
, p. 510 - 513 (2020/01/25)
A chemoenzymatic approach has been developed for the preparation of sertraline, an established anti-depressant drug. Ketoreductases (KREDs) were employed to yield a key chiral precursor. The bioreduction of the racemic tetralone exhibited excellent enantioselectivity (>99 % ee) and diastereomeric ratio (99:1) at 29 % conversion (the maximum theoretical yield is 50 %) after 7 hours. The resulting (S,S)-alcohol was efficiently oxidized to an enantiopure (S)-ketone, an immediate precursor of sertraline, by using sodium hypochlorite as oxidant and 2-azaadamantane N-oxyl (AZADO) as organocatalyst. Alternative routes aiming at the direct biocatalytic amination using imine reductases and transaminases were unsuccessful.
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.
New sertraline analogue, preparation method and applications thereof
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Paragraph 0096-0099, (2020/01/12)
The invention belongs to the technical field of compounds, preparation methods and applications thereof, and specially relates to a sertraline analogue or a pharmaceutically acceptable salt thereof, wherein the sertraline analogue has a structure represented by the following formula (I), and the compound has good pharmaceutical activity compared with sertraline. The invention further provides a preparation method and applications of the compound represented by the formula (I).
End-substituted homoallylic amine derivatives, a preparing method thereof and uses of the derivatives
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, (2018/03/24)
The invention belongs to the field of chemical medicines, and particularly relates to end-substituted homoallylic amine derivatives, a preparing method thereof and uses of the derivatives. In the method, the end-substituted homoallylic amine derivatives are prepared by allowing a 2-aza-allyl anion to participate, in a high regioselectivity manner, an allylation reaction catalyzed by iridium, and by an intramolecular 2-aza-Cope rearrangement reaction. The derivatives can be synthesized efficiently by the method. The method is simple, convenient and feasible. Prepared compounds have extremely high optical purity. The derivatives prepared by the method can be used for preparing Sertraline and Tametraline which are anti-depression medicines and some natural products.
DIPHENYLOXIRANES, PROCESS FOR PREPARATION THEREOF, AND ITS USE IN AN ENANTIOSELECTIVE SYNTHESIS OF (+)-SERTRALINE
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, (2016/06/28)
The present invention discloses substituted diphenyloxiranes and process for synthesis thereof. The present invention also provides a process for production of enantiomerically pure anti-3,3'-diphenylmethyloxirane and anti-3,3'-diphenylpropan- 1,2-diol from racemic anti-3,3'-diphenylmethyloxirane using hydrolytic kinetic resolution. Further it provides a process for preparation of enantioselective (+)- Sertraline from anti-3,3'-diphenylpropan-1,2-diol.
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.
AN ORGANOCATALYTIC ASYMMETRIC SYNTHESIS OF ANTIDEPRESSANTS
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, (2016/06/13)
The present invention relates to a short enantioselective synthesis of 1-amino aryl tetraline compounds of Formula 1 via nucleophilic enamine catalysis using organocatalyst such as proline. wherein R1 and R2 represent independent of each other hydrogen, (un)substituted or substituted amine; R3 and R4 represent independent of each other hydrogen or halogen.
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).
Enantioselective syntheses of (+)-sertraline and (+)-indatraline using lithiation/borylation-protodeboronation methodology
Roesner, Stefan,Casatejada, Javier Mansilla,Elford, Tim G.,Sonawane, Ravindra P.,Aggarwal, Varinder K.
, p. 5740 - 5743 (2011/12/22)
The lithiation/borylation-protodeboronation of a homoallyl carbamate was applied to the synthesis of (+)-sertraline and (+)-indatraline. Due to the presence of the alkene, significant modifications of the methodology were required (use of 12-crown-4, TMSCl, H2O), or a solvent switch to CHCl3, to achieve high yields and high selectivities.
Sertraline racemate and enantiomer: Solid-state characterization, binary phase diagram, and crystal structures
He, Quan,Rohani, Sohrab,Zhu, Jesse,Gomaa, Hassan
experimental part, p. 1633 - 1645 (2011/11/12)
The racemate and enantiomer of sertraline free base were prepared and characterized. The crystalline sertraline enantiomer is relatively less polymorphic compared with the sertraline-HCl salt. The solid-state nature of sertraline racemate was identified to be a racemic compound through a binary melting point phase diagram and spectroscopy analysis. The crystal structures of the racemate and enantiomer were determined to be monoclinic P121/n1 and P21, respectively.
