7076-23-5

Usage

Uses

Used in Pharmaceutical Industry:
(R)-3-(pyrrolidin-2-yl)pyridine is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows it to serve as a building block for the development of new drugs, particularly those targeting the central nervous system.
Used in Chemical Research:
In the field of chemical research, (R)-3-(pyrrolidin-2-yl)pyridine is utilized as a valuable research tool for studying the properties and reactivity of chiral molecules. Its enantiomeric purity can be crucial in understanding the stereochemistry of various chemical reactions and processes.
Used in Insecticide Preparation:
(R)-3-(pyrrolidin-2-yl)pyridine is used as a precursor in the preparation of nicotinoids, which are a class of compounds derived from nicotine. These nicotinoids are employed as insecticides, offering effective pest control in agriculture and other industries.

InChI:InChI=1/C9H12N2/c1-3-8(7-10-5-1)9-4-2-6-11-9/h1,3,5,7,9,11H,2,4,6H2/t9-/m1/s1

Upstream product

• 83023-56-7 3-bromo-5-(pyrrolidin-2-yl)pyridine 
• 5746-86-1 rac-nornicotine 
• 20986-40-7 ethyl 5-bromo-3-pyridinecarboxylate 
• 532-12-7 Myosmine 
• 17708-87-1 5-(pyridin-3-yl)pyrrolidin-2-one 
• 74299-85-7 dimethyl 2-[(pyridin-3-yl)methylidene]malonate 
• 1076199-53-5 2-pyridin-3-ylpyrrolidine-1-carboxylic acid tert-butyl ester 
• 64319-85-3 3-bromo-5-(4,5-dihydro-3H-pyrrol-2-yl)-pyridine 
• 71719-06-7 5-Bromo-3-(2-pyrrolidinyl)pyridine 
• 144635-03-0 (S)-1-(pyridin-3-yl)but-3-en-1-ol 
• 500-22-1 3-pyridinecarboxaldehyde 
• 326818-54-6 3-((R)-1-Azido-but-3-enyl)-pyridine 

Downstream Products

• 25162-00-9 D-nicotine 
• 65-31-6 (+)-Nicotine bitartrate 
• 350820-87-0 (2R)-2-(3-pyridinyl)-1-pyrrolidinebutanoic acid phenylmethyl ester 
• 1346133-09-2 3-chloro-4-[4-[ [ (2R)-2-(3-pyridyl)pyrrolidin-1-yl]methyl]phenoxy]benzamide 

Relevant academic research and scientific papers

PROCESS FOR THE PREPARATION OF (S)-NICOTIN FROM MYOSMINE

A process for synthetically producing (S)-nicotine ([(S)-3-(1 -methylpyrrolidin-2-yl)pyridine]) is provided.

Enantioselective Synthesis of Nicotine via an Iodine-Mediated Hofmann-L?ffler Reaction

An iodine-mediated Hofmann-L?ffler reaction has been developed that enables the first enantioselective synthesis of nicotine based on this synthetic methodology. The effect of the free pyridine core on the involved electrophilic iodine reagents was explored in detail. The final synthesis proceeds under moderate reaction conditions that tolerate the free pyridine core. The same synthetic sequence is also applicable to a number of derivatives with higher substituted pyridine cores, including bipyridine derivatives.

Evaluation of the Edman degradation product of vancomycin bonded to core-shell particles as a new HPLC chiral stationary phase

A modified macrocyclic glycopeptide-based chiral stationary phase (CSP), prepared via Edman degradation of vancomycin, was evaluated as a chiral selector for the first time. Its applicability was compared with other macrocyclic glycopeptide-based CSPs: TeicoShell and VancoShell. In addition, another modified macrocyclic glycopeptide-based CSP, NicoShell, was further examined. Initial evaluation was focused on the complementary behavior with these glycopeptides. A screening procedure was used based on previous work for the enantiomeric separation of 50 chiral compounds including amino acids, pesticides, stimulants, and a variety of pharmaceuticals. Fast and efficient chiral separations resulted by using superficially porous (core-shell) particle supports. Overall, the vancomycin Edman degradation product (EDP) resembled TeicoShell with high enantioselectivity for acidic compounds in the polar ionic mode. The simultaneous enantiomeric separation of 5 racemic profens using liquid chromatography-mass spectrometry with EDP was performed in approximately 3?minutes. Other highlights include simultaneous liquid chromatography separations of rac-amphetamine and rac-methamphetamine with VancoShell, rac-pseudoephedrine and rac-ephedrine with NicoShell, and rac-dichlorprop and rac-haloxyfop with TeicoShell.

Ring Opening of Donor-Acceptor Cyclopropanes with the Azide Ion: A Tool for Construction of N-Heterocycles

A general method for ring opening of various donor-acceptor cyclopropanes with the azide ion through an SN2-like reaction has been developed. This highly regioselective and stereospecific process proceeds through nucleophilic attack on the more-substituted C2 atom of a cyclopropane with complete inversion of configuration at this center. Results of DFT calculations support the SN2 mechanism and demonstrate good qualitative correlation between the relative experimental reactivity of cyclopropanes and the calculated energy barriers. The reaction provides a straightforward approach to a variety of polyfunctional azides in up to 91% yield. The high synthetic utility of these azides and the possibilities of their involvement in diversity-oriented synthesis were demonstrated by the developed multipath strategy of their transformations into five-, six-, and seven-membered N-heterocycles, as well as complex annulated compounds, including natural products and medicines such as (-)-nicotine and atorvastatin. A new world of opportunities: Stereospecific ring opening of donor-acceptor cyclopropanes with the azide ion gives rise to densely functionalized building blocks that are valuable for the assembly of a diverse range of N-heterocycles (see scheme; EDG=electron donating group; EWG=electron withdrawing group). These synthetic opportunities are provided by the simultaneous presence of the N3 group, which reacts as a latent amine or 1,3-dipole, easily modifiable donor and acceptor substituents, as well as the activated CH fragment.

Discovery of aminobenzyloxyarylamides as κ opioid receptor selective antagonists: Application to preclinical development of a κ opioid receptor antagonist receptor occupancy tracer

Arylphenylpyrrolidinylmethylphenoxybenzamides were found to have high affinity and selectivity for κ opioid receptors. On the basis of receptor binding assays in Chinese hamster ovary (CHO) cells expressing cloned human opioid receptors, (S)-3-fluoro-4-(4-((2-(3-fluorophenyl)pyrrolidin-1-yl)methyl) phenoxy)benzamide (25) had a Ki = 0.565 nM for κ opioid receptor binding while having a Ki = 35.8 nM for μ opioid receptors and a Ki = 211 nM for δ opioid receptor binding. Compound 25 was also a potent antagonist of κ opioid receptors when tested in vitro using a [35S]-guanosine 5′O-[3-thiotriphosphate] ([35S]GTP-γ-S) functional assay in CHO cells expressing cloned human opioid receptors. Compounds were also evaluated for potential use as receptor occupancy tracers. Tracer evaluation was done in vivo, using liquid chromatography-tandem mass spectrometry (LC/MS/MS) methods, precluding the need for radiolabeling. (S)-3-Chloro-4-(4-((2-(pyridine-3-yl)pyrrolidin-1-yl)methyl) phenoxy)benzamide (18) was found to have favorable properties for a tracer for receptor occupancy, including good specific versus nonspecific binding and good brain uptake.

Enantioselective, palladium-catalyzed α-arylation of N-Boc pyrrolidine: In situ react IR spectroscopic monitoring, scope, and synthetic applications

A comprehensive study of the enantioselective Pd-catalyzed α-arylation of N-Boc pyrrolidine has been carried out. The protocol involves deprotonation of N-Boc pyrrolidine using s-BuLi/(-)-sparteine in TBME or Et2O at -78 °C, transmetalation with ZnCl2 and Negishi coupling using Pd(OAc)2, t-Bu3P-HBF4 and the aryl bromide. This paper reports several new features including in situ React IR spectroscopic monitoring of the process; use of (-)-sparteine and the (+)-sparteine surrogate to access products with opposite configuration; development of a catalytic asymmetric lithiation-Negishi coupling reaction; extension to a wide range of heteroaromatic bromides; total synthesis of (R)-crispine A, (S)-nicotine and (S)-SIB-1508Y via short synthetic routes; and examples of α-vinylation of N-Boc pyrrolidine using vinyl bromides exemplified by the total synthesis of naturally occurring (+)-maackiamine (thus establishing its configuration as (R)). In this way, the full scope and limitations of the methodology are delineated.

An immunotherapeutic program for the treatment of nicotine addiction: Hapten design and synthesis

People continue to smoke and use tobacco products despite well-established hazardous consequences. The most contributing factor is the addictive nature of nicotine. There is no highly effective treatment for the problem of nicotine dependence. Immunotherapy offers an alternative to conventional approaches. The chemistry necessary for a comprehensive immunopharmacological program is presented. Haptens for the generation of antibodies specific for naturally occurring (S)-nicotine, (S)- and (R)-nornicotine, and the metabolite (S)-cotinine were prepared with high optical purity. Preliminary data for antinicotine antibodies are reported.

A short and efficient synthesis of unnatural (R)-nicotine

A short and efficient synthesis of unnatural (R)-nicotine is described, in which the key step is an intramolecular hydroboration-cycloalkylation of an azido-olefin intermediate. The synthesis is achieved in only four steps, with an overall yield of 51% (or in six steps with an overall yield of 65%). (C) 2000 Elsevier Science Ltd.