3-Methyl-5-(1-methyl-2-pyrrolidinyl)isoxazole

Base Information

• Chemical Name: 3-Methyl-5-(1-methyl-2-pyrrolidinyl)isoxazole
• CAS No.: 147402-53-7
• Molecular Formula: C₉H₁₄N₂O
• Molecular Weight: 166.223
• UNII: B9I6MZL7BW
• DSSTox Substance ID: DTXSID10163711
• Nikkaji Number: J588.286I
• Wikipedia: ABT-418
• Wikidata: Q4650418
• Pharos Ligand ID: R9BV2RCTNVGG
• ChEMBL ID: CHEMBL274525
• Mol file: 147402-53-7.mol

Synonyms:3-methyl-5-(1-methyl-2-pyrrolidinyl)isoxazole;ABT 418;ABT-418

Chemical Property of 3-Methyl-5-(1-methyl-2-pyrrolidinyl)isoxazole

Chemical Property:

• Vapor Pressure: 0.023mmHg at 25°C
• Boiling Point: 249.2°Cat760mmHg
• PKA: 8.89±0.40(Predicted)
• Flash Point: 104.5°C
• PSA: 29.27000
• Density: 1.063g/cm³
• LogP: 1.68760
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 166.110613074
• Heavy Atom Count: 12
• Complexity: 163

Purity/Quality:

99%, ^*data from raw suppliers

ABT-418 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=NOC(=C1)C2CCCN2C
• Isomeric SMILES: CC1=NOC(=C1)[C@@H]2CCCN2C

Technology Process of 3-Methyl-5-(1-methyl-2-pyrrolidinyl)isoxazole

There total 29 articles about 3-Methyl-5-(1-methyl-2-pyrrolidinyl)isoxazole 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: 100.0%

1-methyl-3-(3-methyl-isoxazol-5-yl)-pyrrolidine-2-carbaldehyde → 3-methyl-5-(1-methyl-2(S)-pyrrolidinyl)-isoxazole (147402-53-7,147402-73-1,243119-20-2)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; at 50 ℃;

DOI:10.1016/S0040-4039(99)01059-X

Reference yield: 87.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + A 79814 (147402-52-6,851434-82-7) → (S)-3-methyl-5-(1-methyl-2-pyrrolidinyl)isoxazole (147402-53-7,147402-73-1,243119-20-2)

Guidance literature:

With formic acid; for 2h; Heating;

DOI:10.1002/(SICI)1099-1344(199612)38:12<1099::AID-JLCR934>3.0.CO;2-G

Reference yield: 83.6%

5(S)-(3-methyl-5-isoxazolyl)-2-pyrrolidinone (163849-08-9) → 3-methyl-5-(1-methyl-2(S)-pyrrolidinyl)-isoxazole (147402-53-7,147402-73-1,243119-20-2)

Guidance literature:

With sodium hydroxide; formaldehyd; formic acid; borane; sodium carbonate; In tetrahydrofuran; methanol;

upstream raw materials:

formaldehyd

A 79814

5(S)-(3-methyl-5-isoxazolyl)-2-pyrrolidinone

(S)-2-(3-aminobut-2-enoyl)-N-methylpyrrolidine

Refernces

• 1、 Lin, Nan-Horng. "A short, efficient chiral synthesis of a novel cholinergic channel activator, ABT-418 [(S)-3-methyl-5-(1-methyl-2-pyrrolidinyl)isoxazole], from (S)-pyroglutamic acid". . p. 2563 - 2566. Retrieved 1995.
• 2、 Giard, Thierry,Lasne, Marie-Claire,Plaquevent, Jean-Christophe. "Pyrrolidines bearing a quaternary α-stereogenic center. Part 1: Synthesis of analogs of ABT-418, a powerful nicotinic agonist". . p. 5495 - 5497. Retrieved 2007/10/03.
• 3、 Dolle, Frederic,Dolci, Lilian,Valette, Heric,Bottlaender, Michel,Fournier, Denis,Fuseau, Chantai,Vaufrey, Francoise,Crouzel, Christian. "Synthesis and 11C-labelling of two selective high affinity nicotinic cholinergic agonists for evaluation as radioligands for PET studies". . p. 1099 - 1112. Retrieved 2007/10/03.