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A process for the preparation of (1S,3”R)-quiniclidin-3”-yl-1-phenyl-3,4-dihydro-1H-isoquinolin-2-carboxylate, namely solifenacin, comprising the reaction of a compound of formula (IV) with a compound of formula (V), as herein defined, and the subsequent reaction with 3-quinuclidinol.

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

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Enantiomerically enriched tosyl-protected diarylmethylamines were rapidly prepared by the asymmetric addition of arylboronic acids to N-tosylaldimines under mild conditions in the presence of a catalyst prepared in situ from Rh(I) and a chiral diene ligand. This methodology offers access to diarylmethylamines in good yields with excellent chiral purity at room temperature using MeOH as a solvent and NEt3 as a base. Its synthetic utility was demonstrated by the preparation of (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline (14), an antagonist of the N-methyl-d-aspartate (NMDA) receptor.

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

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Artificial metalloenzymes (ArMs), which combine an abiotic metal cofactor with a protein scaffold, catalyze various synthetically useful transformations. To complement the natural enzymes’ repertoire, effective optimization protocols to improve ArM’s performance are required. Here we report on our efforts to optimize the activity of an artificial transfer hydrogenase (ATHase) using Escherichia coli whole cells. For this purpose, we rely on a self-immolative quinolinium substrate which, upon reduction, releases fluorescent umbelliferone, thus allowing efficient screening. Introduction of a loop in the immediate proximity of the Ir-cofactor afforded an ArM with up to 5-fold increase in transfer hydrogenation activity compared to the wild-type ATHase using purified mutants.

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

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Chemical Research Letters, May 2021. HPLC of Formula: C15H15N, The reaction rate of a catalyzed reaction is faster than the reaction rate of the uncatalyzed reaction at the same temperature.118864-75-8, Name is (S)-1-Phenyl-1,2,3,4-tetrahydroisoquinoline, molecular formula is C15H15N. In a Patent,once mentioned of 118864-75-8

The invention discloses a method of post-processing of the new thorley that, including the synthesis of new thorley thattotal fluid dropping slowly in strengthening acid, adjusting the pH value to 1.0-2.0 temperature after, add water using the extractant; after lowering the aqueous phase by adding saturated sodium carbonate solution to the alkaline, then adding dichloromethane sub-time extraction, extract use of water washing, by adding desiccant drying, position of; the evaporation in the low temperature position to the oily substance solly that our novel alkali. This invention, through optimization of the post-treatment process, the alkali treatment process after new thorley that steps in the use of only two kinds of solvent ISO-propyl ether and dichloromethane, type of the solvent is reduced, it is easy to operate and recycled, the cost is greatly saved. In the hydrochloric acid solly the new return alkali process are not used in a strong base or strong acid, using the saturated NaCO3 solution, the reaction is more moderate, is beneficial to control the temperature, the more important thing is the generation of the isomer is greatly reduced, so that the non-(1S, 3R) isomer of a reduced content of configuration. (by machine translation)

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

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A convenient and general asymmetric transfer hydrogenation of a wide array of 1-aryl-3,4-dihydroisoquinoline derivatives using a [RuIICl(eta6-benzene)TsDPEN] complex in combination with a 5:2 HCOOH-Et3N azeotropic mixture as a hydrogen source was developed. Under mild reaction conditions, the described catalytic transformation secured a practical synthetic access to the corresponding valuable chiral 1-aryltetrahydroisoquinoline units with high atom economy, a broad substrate scope, high isolated yields (up to 97%) and good to excellent enantioselectivities (up to 99% ee). It was found that the stereochemical outcome of the reaction was strongly influenced by both the structure of the catalyst and the substituents present on the substrate. The synthetic utility of the present protocol has been demonstrated through the asymmetric synthesis of several biologically important alkaloids including the antiepileptic drug agent 1c, as well as (-)-nor-cryptostyline alkaloids I and II.

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

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Artificial metalloenzymes (ArMs) based on the incorporation of a biotinylated metal cofactor within a streptavidin (Sav) combine attractive features of both enzymatic and homogeneous catalysis. To speed up their optimization, we present a directed evolution of an artificial transfer hydrogenase (ATHase) based on a streamlined and optimized protocol for the design, overexpression and screening of Sav isoforms. Ten positions have been subjected to mutagenesis to yield two variants with improved catalytic activity and selectivity for the reduction of cyclic imines, along with greater stability in a biphasic medium.

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

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The title compounds (S)-(+)-8 and (R)-(-)-8 have been prepared by an asymmetric synthesis that is based on stereoselective additions to the chiral N-acylisoquinoliniumion 3. The absolute configuration of these compounds has been determined by an X-ray analysis performed on the intermediate 5. According to the results of this study the stereochemical assignment for (S)-(+)-8 and (R)-(-)-8 described in the literature has to be revised.

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

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A catalysed two-way enantioselective synthesis of chiral tetrahydroisoquinoline method, the catalyzing system is iridium chiral double phosphine complexes. The use of sole chiral source, to the reaction system through the achiral additive consumption of N – bromosuccinimide adjusting, realizes the simple and easily obtained 3, 4 – ISO-quinoline substrate of the asymmetric hydrogenation. The method utilizes a sole chiral source respectively to obtain the corresponding chiral tetrahydroisoquinoline of two enantiomers, its enantiomeric excess highest respectively reaches 89% (S) and 98% (R). The operation of the invention is simple and practical and easy, simple and easy to obtain raw materials, catalyst commercial available, mild reaction conditions, high yield, high enantioselectivity. In addition, only through non-chiral additive conditions, can obtain the tetrahydroisoquinoline of two enantiomers, successfully avoids the two different configuration ligand. (by machine translation)

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

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A concise deracemization of racemic secondary and tertiary amines with a tetrahydroisoquinoline core has been successfully realized by orchestrating a redox process consisted of N-bromosuccinimide oxidation and iridum-catalyzed asymmetric hydrogenation. This compatible redox combination enables one-pot, single-operation deracemization to generate chiral 1-substituted 1,2,3,4-tetrahydroisoquinolines with up to 98% ee in 93% yield, offering a simple and scalable synthetic technique for chiral amines directly from racemic starting materials.

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

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New Advances in Chemical Research in 2021. In homogeneous catalysis, the catalyst is in the same phase as the reactant. The number of collisions between reactants and catalyst is at a maximum.In a patent, 118864-75-8, name is (S)-1-Phenyl-1,2,3,4-tetrahydroisoquinoline, introducing its new discovery. name: (S)-1-Phenyl-1,2,3,4-tetrahydroisoquinoline

A new method for the asymmetric synthesis of 1-substituted tetrahydroisoquinolines is presented. It is based on stereoselective addition reactions of organometallic compounds to the intermediate N-acylimimum ion 6, which is provided with an N-acyl group as a chiral auxiliary. In addition reactions with organomagnesium and organozinc reagents diastereoselectivities from 70:30 to 95:5 (for 7/8) were observed with the zinc reagents in general leading to markedly improved stereoselectivities. By catalytic hydrogenation of 7 and 8 and after removal of the chiral auxiliary the target compounds 11 and 12 were obtained. The enantiomerically pure 11c-g and 12c-g (ee > 99%), 1-aryltetrahydroisoquinolines, were evaluated for their affinity to the PCP [1-(1-phenylcyclohexyl)piperidine] binding site of the NMDA (N-methyl D-aspartate) receptor. In each case the enantiomers 11 exhibited a higher affinity than those of 12, with the potencies of the enantiomers differing by a factor of 4 (11/12g) to 27 (11/12c). The absolute configuration of the more potent enantiomers 11 is in accordance with the stereochemical requirement found for FR 115427 (3) which is a close analogue.

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