(R)-3-(Pyrrolidin-2-ylmethoxy)pyridine

Base Information

• Chemical Name: (R)-3-(Pyrrolidin-2-ylmethoxy)pyridine
• CAS No.: 161416-94-0
• Molecular Formula: C10H14N2O
• Molecular Weight: 178.23
• DSSTox Substance ID: DTXSID20443672
• Wikidata: Q72505361
• ChEMBL ID: CHEMBL440195
• Mol file: 161416-94-0.mol

Synonyms:(R)-3-(Pyrrolidin-2-ylmethoxy)pyridine;161416-94-0;3-[[(2R)-pyrrolidin-2-yl]methoxy]pyridine;3-[(2R)-2-PYRROLIDINYLMETHOXY]PYRIDINE;SCHEMBL905236;CHEMBL440195;DTXSID20443672;AKOS016845573;AC-22429;CS-0447607

Chemical Property of (R)-3-(Pyrrolidin-2-ylmethoxy)pyridine

Chemical Property:

• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.519
• Boiling Point: 300.767 °C at 760 mmHg
• PKA: 9.98±0.10(Predicted)
• Flash Point: 135.699 °C
• PSA: 34.15000
• Density: 1.064 g/cm³
• LogP: 1.54120
• Storage Temp.: 2-8°C
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 178.110613074
• Heavy Atom Count: 13
• Complexity: 152

Purity/Quality:

98%min ^*data from raw suppliers

(R)-3-(Pyrrolidin-2-ylmethoxy)pyridine 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(NC1)COC2=CN=CC=C2
• Isomeric SMILES: C1C[C@@H](NC1)COC2=CN=CC=C2

Technology Process of (R)-3-(Pyrrolidin-2-ylmethoxy)pyridine

There total 9 articles about (R)-3-(Pyrrolidin-2-ylmethoxy)pyridine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

3-(1-t-butoxycarbonyl-2-(R)-pyrrolidinylmethoxy) pyridine → 3-(2-(R)-pyrrolidinylmethoxy)pyridine (161416-94-0)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 2.5h; Ambient temperature;

DOI:10.1021/jm9506884

Reference yield: 31.0%

(S)-2-(pyridin-3-yloxymethyl)pyrrolidine-1-carboxylic acid tert-butyl ester (161417-33-0) → 3-(2-(S)-pyrrolidin-2-ylmethoxy)pyridine (161416-57-5,161416-94-0)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 3h; Ambient temperature;

DOI:10.1021/jm9506884

Reference yield:

N-(tert-butoxycarbonyl)-L-prolinol (69610-40-8) → 3-(2-(S)-pyrrolidin-2-ylmethoxy)pyridine (161416-57-5,161416-94-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 100 percent / pyridine / CH₂Cl₂ / 20 °C

2.1: NaH / tetrahydrofuran / 0.67 h / 0 - 20 °C

2.2: 61 percent / tetrahydrofuran / 24 h / Heating

3.1: CF₃CO₂H / CH₂Cl₂ / 0.25 h / 0 °C

With pyridine; sodium hydride; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm0506625

upstream raw materials:

(S)-2-(pyridin-3-yloxymethyl)pyrrolidine-1-carboxylic acid tert-butyl ester

N-(tert-butoxycarbonyl)-L-prolinol

(S)-tert-butyl 2-((tosyloxy)methyl)pyrrolidine-1-carboxylate

3-HYDROXYPYRIDINE

Refernces

• 1、 -. "Preparation of heterocyclic ethers as neuronal nicotinic receptor ligands.". . . Retrieved 2008/06/13.
• 2、 Abreo, Melwyn A.,Lin, Nan-Horng,Garvey, David S.,Gunn, David E.,Hettinger, Ann-Marie,Wasicak, James T.,Pavlik, Patricia A.,Martin, Yvonne C.,Donnelly-Roberts, Diana L.,Anderson, David J.,Sullivan, James P.,Williams, Michael,Arneric, Stephen P.,Holladay, Mark W.. "Novel 3-pyridyl ethers with subnanomolar affinity for central neuronal nicotinic acetylcholine receptors". . p. 817 - 825. Retrieved 2007/10/03.