71962-74-8Relevant articles and documents
Development of an efficient synthesis for a nipecotate-containing immunopotentiator
Moher, Eric D.,Tripp, Allie E.,Creemer, Lawrence C.,Vicenzi, Jeffrey T.
, p. 593 - 596 (2004)
The preparation of Elanco Animal Health immunopotentiator (S)-ethyl-1-(2-thiopheneacetyl)-3-piperidinecarboxylate (1) is described. The synthesis includes a new resolution of racemic ethyl nipecotate with dibenzoyl-L-tartaric acid. The resolved salt is found to couple directly with commercially available 2-thiopheneacetyl chloride under environmentally friendly Schotten-Baumann conditions to afford the amide in high yield. The final product is an oil which is purified by wiped film evaporative distillation.
A one-step, enantioselective reduction of ethyl nicotinate to ethyl nipecotinate using a constrained, chiral, heterogeneous catalyst
Raynor,Thomas,Raja,Johnson,Bell,Mantle
, p. 1925 - 1926 (2000)
A chiral catalyst derived from 1,1'-bis(diphenylphosphino)-ferrocene and anchored within MCM-41 displays remarkable increases in both enantioselectivity and activity, in the hydrogenation of ethyl nicotinate to ethyl nipecotinate, when compared to an analogous homogeneous model compound.
Electrolytic synthesis of nipecotic acid ethyl ester
Muldakhmetov,Gazaliev,Kirilyus,Fazylov
, p. 1087 - 1089 (2007)
An electrolytic method was suggested for the synthesis of nipecotic acid ethyl ester in a diaphragm electrolytic cell on a copper cathode in aqueous-alcoholic alkali solution.
Br?nsted Acid Catalyzed Cyclization of Aminodiazoesters with Aldehydes to 3a'Carboxylatea'Na'Heterocycles
Jiao, Yang,Chen, Anrong,Yu, Bangkui,Huang, Hanmin
supporting information, p. 6031 - 6034 (2020/09/01)
A Br?nsted acid catalyzed cyclization of aminodiazoesters with aldehydes is described. This reaction features broad substrate generality and functional group compatibility, affording a wide range of 5a'7-membered 3-carboxylate-N-heterocycles containing different functional groups. The title products are able to be further elaborated through simple functional group transformations to produce synthetically useful N-heterocycles.
Cobalt-bridged secondary building units in a titanium metal-organic framework catalyze cascade reduction of N-heteroarenes
Feng, Xuanyu,Song, Yang,Chen, Justin S.,Li, Zhe,Chen, Emily Y.,Kaufmann, Michael,Wang, Cheng,Lin, Wenbin
, p. 2193 - 2198 (2019/02/20)
We report here a novel Ti3-BPDC metal-organic framework (MOF) constructed from biphenyl-4,4′-dicarboxylate (BPDC) linkers and Ti3(OH)2 secondary building units (SBUs) with permanent porosity and large 1D channels. Ti-OH groups from neighboring SBUs point toward each other with an O-O distance of 2 ?, and upon deprotonation, act as the first bidentate SBU-based ligands to support CoII-hydride species for effective cascade reduction of N-heteroarenes (such as pyridines and quinolines) via sequential dearomative hydroboration and hydrogenation, affording piperidine and 1,2,3,4-tetrahydroquinoline derivatives with excellent activity (turnover number ～ 1980) and chemoselectivity.
Polysilane-Immobilized Rh-Pt Bimetallic Nanoparticles as Powerful Arene Hydrogenation Catalysts: Synthesis, Reactions under Batch and Flow Conditions and Reaction Mechanism
Miyamura, Hiroyuki,Suzuki, Aya,Yasukawa, Tomohiro,Kobayashi, Shu
supporting information, p. 11325 - 11334 (2018/09/06)
Hydrogenation of arenes is an important reaction not only for hydrogen storage and transport but also for the synthesis of functional molecules such as pharmaceuticals and biologically active compounds. Here, we describe the development of heterogeneous Rh-Pt bimetallic nanoparticle catalysts for the hydrogenation of arenes with inexpensive polysilane as support. The catalysts could be used in both batch and continuous-flow systems with high performance under mild conditions and showed wide substrate generality. In the continuous-flow system, the product could be obtained by simply passing the substrate and 1 atm H2 through a column packed with the catalyst. Remarkably, much higher catalytic performance was observed in the flow system than in the batch system, and extremely strong durability under continuous-flow conditions was demonstrated (>50 days continuous run; turnover number >3.4 × 105). Furthermore, details of the reaction mechanisms and the origin of different kinetics in batch and flow were studied, and the obtained knowledge was applied to develop completely selective arene hydrogenation of compounds containing two aromatic rings toward the synthesis of an active pharmaceutical ingredient.
Process intensification for the continuous flow hydrogenation of ethyl nicotinate
Ouchi, Takashi,Battilocchio, Claudio,Hawkins, Joel M.,Ley, Steven V.
supporting information, p. 1560 - 1566 (2015/02/19)
Here we report a process intensification study for the selective, partial, and full hydrogenation of ethyl nicotinate using a trickle bed reactor for meso-flow transformations (HEL FlowCAT). The process achieved a throughput of 1219 g d-1 (78 g h-1 of product per g of active catalyst) for the partial hydrogenation to ethyl 1,4,5,6-tetrahydropyridine-3-carboxylate, whereas the productivity for the full hydrogenation process reached a 1959 g d-1 of throughput (408 g h-1 of product per g of active catalyst) on this laboratory-scale flow chemistry platform.
Continuous flow hydrogenation of functionalized pyridines
Irfan, Muhammed,Petricci, Elena,Glasnov, Toma N.,Taddei, Maurizio,Kappe, C. Oliver
experimental part, p. 1327 - 1334 (2009/07/19)
The heterogeneous hydrogenation of substituted pyridines has been accomplished by employing a continuous flow hydrogenation device that incorporates in situ hydrogen generation by electrolysis of H20 and pre-packed catalyst cartridges. In general, the hydrogenation reactions proceeded smoothly regardless of the supported precious metal catalyst (Pd/C, Pt/C, or Rh/C). By using 30-80 bar of hydrogen pressure at 60-80 °C full conversion was typically achieved in all cases at a flow rate of 0.5 mL min -1, providing the corresponding piperidines in high yields. For disubstituted pyr idines, variations in stereoselectivity were observed depending on both the metal catalyst and the temperature/ pressure of the hydrogenation reaction. For ethyl nicotinate the selectivity between partial and full hydrogenation could be tuned depending on the hydrogen pressure, solvent, and the choice of supported metal catalyst. Changing the hydrogen source from H20 to D2C) allowed the preparation of de-uteriated derivatives. Wiley-VCH Verlag GmbH & Co. KGaA.
N-BENZYL-3-PHENYL-3-HETEROCYCLYL-PROPIONAMIDE COMPOUNDS AS TACHYKININ AND/ OR SEROTONIN REUPTAKE INHIBITORS
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Page 44, (2010/02/06)
The present invention relates to heterocyclic derivatives of formula (1) wherein R1 represents a 5 or 6 membered heteroaryl group, in which the 5-membered heteroaryl group contains at least one heteroatom selected from oxygen, sulphur or nitrogen and the 6-membered heteroaryl group contains from 1 to 3 nitrogen atoms, or R1 represents a 4,5 or 6 membered heterocyclic group, wherein saids 5 or 6 membered heteroaryl or the 4,5 or 6 membered heterocyclic group may optionally be substituted by one to three substituents, which may be the same or different, selected from (CH2)pR6, wherein p is zero or an integer from 1 to 4 and wherein R and R2- R6 are each as defined in the description and pharmaceutically acceptable salts and solvates thereof; process for their preparation and their use in the treatment of conditions mediated by tachykinins and/or by selective inhibition of serotonin reuptake transporter protein.
Enantioselective homogeneous hydrogenation of monosubstituted pyridines and furans
Studer, Martin,Wedemeyer-Exl, Christina,Spindler, Felix,Blaser, Hans-Ulrich
, p. 1335 - 1343 (2007/10/03)
The first case of an enantioselective hydrogenation of monosubstituted pyridines and furans with homogeneous rhodium diphosphine catalysts with low but significant enantioselectivities and catalyst activities is reported. Best enantioselectivities (ees of 24-27%) were obtained for the hydrogenation of 2-and 3-pyridine carboxylic acid ethyl ester and 2-furan carboxylic acid with catalysts prepared in situ from [Rh(nbd)2]BF4 and the chiral ligands diop, binap, or ferrocenyl diphosphines of the josiphos type. Turnover numbers (ton) were in the order of 10-20, turnover frequencies (tof) usually 1-2 h-1. Diphosphines giving 6-or 7-ring chelates led to higher ees than 1,2-diphosphines; otherwise, no clear correlation between ligand properties and catalytic performance was found. In some experiments black precipitates were observed at the end of the reaction, indicating the decomposition of the homogeneous catalysts for certain ligand/metal/ substrate combinations.
