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Hydrotalcite catalyzed N-alkylation: A practical greener approach towards Carbon-Nitrogen bond formation

Main driving force of this research work is to focus 9th principle (Catalysis) out of 12 principles of green chemistry so as to protect environment concerned with the reduction in generation of carbon dioxide, one of the green house gas. An innovative development of chemical pathway regarding N-alkylation reaction carried out by adding and recycling only catalytic amount of Hydrotalcite as solid base instead of stoichiometric amount, as per prior art techniques, has attempted. Synthesis of 3 amines, important Active Pharmaceutical Ingredients (APIs) and their intermediates, maintaining the same quality attributes resulting in to minimum generation of carbon dioxide are described. These concept is designed, synthesized, characterized, quantified and compared using ?Carbon Efficiency?, a Green Chemistry Metrics, with already reported work to prove its sustainability. It is industrially advantageous by getting improvement in carbon efficiency and yield as outcome. Here we show a practical greener approach towards Carbon ? Nitrogen bond formation with the help of calculation of Carbon efficiency and rate of reaction for first time.

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Reference£º
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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NOVEL PROCESS FOR THE PREPARATION OF SOLIFENACIN SUCCINATE

The present invention relates to a process for the preparation of Solifenacin succinate by condensing a compound of formula (IVb) with (RS)-3-quinuclidinol, wherein, R represents methyl, ethyl, isopropyl; to produce a diastereomeric mixture of (1S)-3,4-dihydro-1-phenyl-2(1H)-isoquinolinecarboxylic acid (3RS)-1-azabicyclo[2.2.2]oct-3-yl ester, which is treated with succinic acid in a solvent or mixture of solvents to produce optically pure Solifenacin succinate, Formula (X).

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1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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PROCESS FOR PREPARING CHEMICALLY AND CHIRALLY PURE SOLIFENACIN BASE AND ITS SALTS

The present invention provides improved processes for preparing chemically and chirally pure Solifenacin base. The present invention also provides for a composition comprising of a salt of Solifenacin having at least 98 % purity. The present invention also disclose certain new salts of Solifenacin as well as well as new polymorphic forms of Solifenacin hydrochloride and Solifenacin oxalate, in pure form.

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Quinuclidine derivatives and medicinal composition thereof

Quinuclidine derivatives represented by general following general formula (I), salts, N-oxides or quaternary ammonium salts thereof, and medicinal compositions containing the same. STR1 The compound has an antagonistic effect on muscarinic M 3 receptors and is useful as a preventive or remedy for urologic diseases, respiratory diseases or digestive diseases.

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Asymmetric synthesis of 1-aryl-1,2,3,4-tetrahydroisoquinolines part 1: Addition of chiral phenylacetaldehyde acetals to acylimines

The stereoselectivity in the addition of the enantiomerically pure (2-bromophenyl)acetaldehyde acetals 3a-g to the acylimines 4a,b is investigated. Based on this reaction a novel asymmetric synthesis for the 1-phenyl-tetrahydroisoquinoline 8 is elaborated.

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Synthesis and antimuscarinic properties of quinuclidin-3-yl 1,2,3,4-tetrahydroisoquinoline-2-carboxylate derivatives as novel muscarinic receptor antagonists

In the course of continuing efforts to develop potent and bladder-selective muscarinic M3 receptor antagonists, quinuclidin-3-yl 1-aryl-1,2,3,4-tetrahydroisoquinoline-2-carboxylate derivatives and related compounds were designed as conformationally restricted analogues of quinuclidin-3-yl benzhydrylcarbamate (8). Binding assays with rat muscarinic receptor subtypes revealed that the quinuclidin-3-yl 1-aryl-1,2,3,4- tetrahydroisoquinoline-2-carboxylate derivatives showed high affinities for the M3 receptor, and selectivity for the M3 receptor over the M2 receptor. Of these derivatives, (+)-(1S,3’R)-quinuclidin-3′-yl 1-phenyl-l,2,3,4-tetrahydroisoquinoline-2-carboxylate monohydrochloride (9b) exhibited almost the same inhibitory activity against bladder contraction to that of oxybutynin (1), and more than 10-fold selectivity for bladder contraction versus salivary secretion, demonstrating that 9b may be useful for the treatment of symptoms associated with overactive bladder without having side effects such as dry mouth.

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Directed Evolution of an Artificial Imine Reductase

Artificial metalloenzymes, resulting from incorporation of a metal cofactor within a host protein, have received increasing attention in the last decade. The directed evolution is presented of an artificial transfer hydrogenase (ATHase) based on the biotin-streptavidin technology using a straightforward procedure allowing screening in cell-free extracts. Two streptavidin isoforms were yielded with improved catalytic activity and selectivity for the reduction of cyclic imines. The evolved ATHases were stable under biphasic catalytic conditions. The X-ray structure analysis reveals that introducing bulky residues within the active site results in flexibility changes of the cofactor, thus increasing exposure of the metal to the protein surface and leading to a reversal of enantioselectivity. This hypothesis was confirmed by a multiscale approach based mostly on molecular dynamics and protein?ligand dockings.

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A succinic acid thorley that new preparation method (by machine translation)

The present invention relates to succinic acid thorley that new preparation, which belongs to the technical field of the preparation of the raw material. The technical scheme of the present invention is: a kind of new succinic acid thorley that new preparation method, is characterized in that R – 3 – the quinine is mellow, S – 1 – phenyl – 1, 2, 3, 4 – tetrahydroisoquinoline as raw materials, to solid phosgene and substituted phosphine oxide of the reaction product is condensing agent, process for preparing Solley that new. By succinic acid and get thorley that new. The beneficial effect of the present invention is: provides a simple operation, the reaction condition is relatively moderate, and is suitable for industrial scale production of succinic acid thorley that new preparation method. (by machine translation)

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Enantioselective synthesis of 1-aryltetrahydroisoquinolines

(Figure presented) 1-Aryltetrahydroisoquinolines (1-arylTHIQs) are important structural motifs in many alkaloids and biologically active compounds. Ligand 2a promotes the enantioselective addition of arylzinc reagents to 3,4-dihydroisoquinoline N-oxide to yield (S)-1-arylTHIQs in 97-99% ee. Pinacol arylboronic esters are the optimal precursors for the arylzinc reagents. This method is applied to the enantioselective synthesis of Solifenacin.

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SOLIFENACIN-CONTAINING COMPOSITION

To provide a novel method for producing a composition comprising solifenacin or a salt thereof, and a composition comprising solifenacin or a salt thereof as produced by the method, wherein an optionally substituted lower alkyl is added to the 2-position of the quinuclidine of solifenacin. The composition of the present invention contains a highly pure solifenacin, while the unexpected compounds specific to the method in an extremely low content, so that it has very preferable properties as a bulk for pharmaceutical products.

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Tetrahydroisoquinoline – Wikipedia,
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