N-(6-Fluoropyridine-3-carbonyl)-L-proline

Base Information

• Chemical Name: N-(6-Fluoropyridine-3-carbonyl)-L-proline
• CAS No.: 123412-44-2
• Molecular Formula: C₁₁H₁₁FN₂O₃
• Molecular Weight: 238.218
• DSSTox Substance ID: DTXSID70562327
• Mol file: 123412-44-2.mol

Synonyms:123412-44-2;N-(6-Fluoropyridine-3-carbonyl)-L-proline;(S)-1-(6-Fluoronicotinoyl)pyrrolidine-2-carboxylic acid;(2S)-1-(6-FLUOROPYRIDINE-3-CARBONYL)PYRROLIDINE-2-CARBOXYLIC ACID;1-(6-Fluoropyridine-3-carbonyl)-L-proline;DTXSID70562327

Chemical Property of N-(6-Fluoropyridine-3-carbonyl)-L-proline

Chemical Property:

• Vapor Pressure: 4.4E-10mmHg at 25°C
• Refractive Index: 1.585
• Boiling Point: 481.5°Cat760mmHg
• Flash Point: 245°C
• PSA: 70.50000
• Density: 1.43g/cm³
• LogP: 0.84780
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 238.07537038
• Heavy Atom Count: 17
• Complexity: 324

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(N(C1)C(=O)C2=CN=C(C=C2)F)C(=O)O
• Isomeric SMILES: C1C[C@H](N(C1)C(=O)C2=CN=C(C=C2)F)C(=O)O

Technology Process of N-(6-Fluoropyridine-3-carbonyl)-L-proline

There total 4 articles about N-(6-Fluoropyridine-3-carbonyl)-L-proline 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: 67.0%

6-fluoronicotinoyl chloride (65352-94-5) + L-proline (147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7) → N-<(2-fluoropyridin-5-yl)carbonyl>pyrrolidine-2-carboxylic acid (123412-44-2)

Guidance literature:

With sodium hydroxide; In water; acetone; for 15h; Ambient temperature;

DOI:10.1021/jm00168a021

Reference yield:

(5-methyl-pyridin-2-yl)amine (1603-41-4) → N-<(2-fluoropyridin-5-yl)carbonyl>pyrrolidine-2-carboxylic acid (123412-44-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) NaNO₂, 2.) 48percent aq. HBF₄

2: 45 percent / KMnO₄ / H₂O / 4.5 h / 100 °C

3: 86 percent / thionyl chloride / 25 h / Heating

4: 67 percent / NaOH / H₂O; acetone / 15 h / Ambient temperature

With sodium hydroxide; potassium permanganate; tetrafluoroboric acid; thionyl chloride; sodium nitrite; In water; acetone;

DOI:10.1021/jm00168a021

Reference yield:

2-fluoro-5-methylpyridine (2369-19-9) → N-<(2-fluoropyridin-5-yl)carbonyl>pyrrolidine-2-carboxylic acid (123412-44-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 45 percent / KMnO₄ / H₂O / 4.5 h / 100 °C

2: 86 percent / thionyl chloride / 25 h / Heating

3: 67 percent / NaOH / H₂O; acetone / 15 h / Ambient temperature

With sodium hydroxide; potassium permanganate; thionyl chloride; In water; acetone;

DOI:10.1021/jm00168a021

upstream raw materials:

6-fluoronicotinoyl chloride

L-proline

(5-methyl-pyridin-2-yl)amine

2-fluoro-5-methylpyridine