(S)-3-(Azetidin-2-ylmethoxy)pyridine

Base Information

• Chemical Name: (S)-3-(Azetidin-2-ylmethoxy)pyridine
• CAS No.: 161416-98-4
• Molecular Formula: C₉H₁₂N₂O
• Molecular Weight: 164.207
• Nikkaji Number: J720.813H
• Wikidata: Q27074089
• Pharos Ligand ID: PDWX7X1T3FZY
• ChEMBL ID: CHEMBL59986
• Mol file: 161416-98-4.mol

Synonyms:3-(2-azetidinylmethoxy)pyridine;A 159470;A 85380;A-159470;A-85380

Chemical Property of (S)-3-(Azetidin-2-ylmethoxy)pyridine

Chemical Property:

• PSA: 34.15000
• LogP: 1.15110
• Solubility.: H2O: 10 mg/mL
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 164.094963011
• Heavy Atom Count: 12
• Complexity: 141

Purity/Quality:

99% ^*data from raw suppliers

A-85380 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CNC1COC2=CN=CC=C2
• Isomeric SMILES: C1CN[C@@H]1COC2=CN=CC=C2

Technology Process of (S)-3-(Azetidin-2-ylmethoxy)pyridine

There total 4 articles about (S)-3-(Azetidin-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: 80.0%

(S)-3-(1-benzyloxycarbonyl-2-azetidinylmethoxy)pyridine → 3-(2-(S)-azetidinylmethoxy)pyridine (161416-98-4)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; at 20 ℃; for 0.5h; under 760.051 Torr;

DOI:10.1016/j.tetlet.2004.03.061

Reference yield:

(S)-tert-butyl 2-((pyridin-3-yloxy)methyl)azetidine-1-carboxylate (161417-31-8) → 3-(2-(S)-azetidinylmethoxy)pyridine (161416-98-4)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 18h; gradually warming from 0 deg to RT;

DOI:10.1021/jm9506884

Reference yield:

3-HYDROXYPYRIDINE (109-00-2) → 3-(2-(S)-azetidinylmethoxy)pyridine (161416-98-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

1.2: 24 h / Inert atmosphere; Reflux

2.1: trifluoroacetic acid / dichloromethane / 0.25 h / 0 °C / Inert atmosphere

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

DOI:10.1016/j.bmcl.2011.03.015

upstream raw materials:

(S)-tert-butyl 2-((pyridin-3-yloxy)methyl)azetidine-1-carboxylate

3-HYDROXYPYRIDINE

Downstream raw materials:

(S)-2-(1-(4-methoxybenzyl)-2-oxo-5-(2-((pyridin-3-yloxy)methyl)azetidin-1-ylsulfonyl)indolin-3-ylidene)malononitrile

(S)-2-(1-(4-(2-fluoroethoxy)benzyl)-2-oxo-5-(2-((pyridin-3-yloxy)methyl)azetidin-1-ylsulfonyl)indolin-3-ylidene)malononitrile

(S)-1-(4-methoxybenzyl)-5-(2-((pyridin-3-yloxy)methyl)azetidin-1-ylsulfonyl)indoline-2,3-dione

(S)-1-(4-(2-fluoroethoxy)benzyl)-5-(2-((pyridin-3-yloxy)methyl)azetidin-1-ylsulfonyl)indoline-2,3-dione

Refernces

• 1、 Brenner, Eric,Baldwin, Ronald M.,Tamagnan, Gilles. "Synthesis of a new precursor to the nicotinic receptor tracer 5-IA-85380 precursor using trimethylsilyl iodide as deblocking agent". . p. 3607 - 3610. Retrieved 2007/10/03.
• 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.