3-[(2S)-pyrrolidin-2-yl]pyridine

Base Information

• Chemical Name: 3-[(2S)-pyrrolidin-2-yl]pyridine
• CAS No.: 494-97-3
• Molecular Formula: C9H12N2
• Molecular Weight: 148.208
• Hs Code.: 2933990090
• European Community (EC) Number: 621-530-4
• UNII: 83H6L5QD8Z
• DSSTox Substance ID: DTXSID7075420
• Nikkaji Number: J6.079H
• Wikidata: Q28466251
• Metabolomics Workbench ID: 51673
• ChEMBL ID: CHEMBL6200
• Mol file: 494-97-3.mol

Synonyms:3-(2-pyrrolidinyl)pyridine;nornicotine;nornicotine tartrate, (S)-(R-(R*,R*))-isomer;nornicotine, (R)-isomer;nornicotine, (S)-isomer

Chemical Property of 3-[(2S)-pyrrolidin-2-yl]pyridine

Chemical Property:

• Vapor Pressure: 0.007mmHg at 25°C
• Refractive Index: nD20 1.5378
• Boiling Point: 269.999°C at 760 mmHg
• PKA: 9.09±0.10(Predicted)
• Flash Point: 111.291°C
• PSA: 24.92000
• Density: 1.043g/cm³
• LogP: 1.83490
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility.: Acetonitrile (Slightly), Chloroform (Slightly), Methanol (Sparingly)
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 148.100048391
• Heavy Atom Count: 11
• Complexity: 125

Purity/Quality:

98%Min ^*data from raw suppliers

Nornicotine-d4 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Plant Toxins
• Canonical SMILES: C1CC(NC1)C2=CN=CC=C2
• Isomeric SMILES: C1C[C@H](NC1)C2=CN=CC=C2
• Uses: (S)-Nornicotine is a metabolite of Nicotine (N412420). Can catalyze aqueous aldol reactions. Agricultural or horticultural insecticide.

Technology Process of 3-[(2S)-pyrrolidin-2-yl]pyridine

There total 53 articles about 3-[(2S)-pyrrolidin-2-yl]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: 95.0%

(S)-1-(2,3,4,6-Tetra-O-pivaloyl-β-D-galactopyranosyl)-2-(3-pyridyl)pyrrolidine (252005-64-4) → 2,3,4,6-Tetra-O-pivaloyl-α/β-D-galactopyranose (135865-76-8,135865-81-5,144102-44-3,148968-87-0,150737-36-3) + nornicotine (494-97-3,13450-58-3)

Guidance literature:

In hydrogenchloride; methanol;

DOI:10.1016/S0040-4039(99)01606-8

Reference yield: 85.0%

(S)-3-(1-azido-but-3-enyl)pyridine (314280-29-0) → nornicotine (494-97-3,13450-58-3)

Guidance literature:

With bis(cyclohexanyl)borane; In tetrahydrofuran; at -15 - 20 ℃; for 12h;

DOI:10.1021/jo010386b

Reference yield: 72.0%

(S)-3-(1,4-dichlorobutyl)pyridine → nornicotine (494-97-3,13450-58-3)

Guidance literature:

With ammonium hydroxide; potassium carbonate; at 60 ℃; for 5h; Reagent/catalyst;

upstream raw materials:

rac-nornicotine

nicotin

(S)-5-bromo-3-(1H-2-pyrrolidinyl)pyridine

(S)-1-(2,3,4,6-Tetra-O-pivaloyl-β-D-galactopyranosyl)-2-(3-pyridyl)pyrrolidine

Downstream raw materials:

nicotin

N-acetylnornicotine

N'-ethyl-S-nornicotine

3-((S)-1-allyl-pyrrolidin-2-yl)-pyridine

Refernces

• 1、 -. "Preparation method of chiral nicotine synthesized by chiral tert-butyl sulfinamide". . . Retrieved 2021/09/29.
• 2、 -. "PROCESS FOR THE PREPARATION OF (S)-NICOTIN FROM MYOSMINE". Page/Page column 13-17. . Retrieved 2020/06/05.