7076-23-5

Basic information

• Product Name: (R)-3-(pyrrolidin-2-yl)pyridine
• Synonyms: (R)-3-(pyrrolidin-2-yl)pyridine;(R)-Nornicotine;3-[(R)-Pyrrolidin-2-yl]pyridine;Einecs 230-373-7;L-Nornicotine hydrochloride;Nornicotine, hydrochloride, (-)-;3-[(2R)-pyrrolidin-2-yl]pyridine;Pyridine, 3-(2R)-2-pyrrolidinyl-
• CAS NO: 7076-23-5
• Molecular Formula: C₉H₁₂N₂
• Molecular Weight: 148.20498
• EINECS: 230-373-7
• Mol File: 7076-23-5.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 270°C at 760 mmHg
• Flash Point: 111.3°C
• Appearance: /
• Density: 1.042g/cm³
• Vapor Pressure: 0.00702mmHg at 25°C
• Refractive Index: 1.536
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility: Acetonitrile (Slightly), Chloroform (Slightly)
• PKA: 9.09±0.10(Predicted)
• Stability: Light Sensitive
• CAS DataBase Reference: (R)-3-(pyrrolidin-2-yl)pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-3-(pyrrolidin-2-yl)pyridine(7076-23-5)
• EPA Substance Registry System: (R)-3-(pyrrolidin-2-yl)pyridine(7076-23-5)

Safety Data

• Hazardous Substances Data: 7076-23-5(Hazardous Substances Data)

Usage

Description

(R)-3-(pyrrolidin-2-yl)pyridine is an organic compound characterized by its unique molecular structure, featuring a pyridine ring with a pyrrolidin-2-yl group attached at the 3rd position. This chiral molecule exists in two enantiomeric forms, with the (R)-configuration being of particular interest due to its potential applications in various fields.

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

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

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 articles and documents

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.

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.

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.