4'-fluorococaine

Base Information

• Chemical Name: 4'-fluorococaine
• CAS No.: 134507-62-3
• Molecular Formula: C17H20FNO4
• Molecular Weight: 321.3434
• UNII: 6045353J3C
• DSSTox Substance ID: DTXSID10928640
• Nikkaji Number: J373.270C
• Wikipedia: 4%E2%80%B2-Fluorococaine
• Mol file: 134507-62-3.mol

Synonyms:8-Azabicyclo[3.2.1]octane-2-carboxylicacid, 3-[(4-fluorobenzoyl)oxy]-8-methyl-, methyl ester, [1R-(exo,exo)]-;

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Chemical Property of 4'-fluorococaine

Chemical Property:

• Boiling Point: 398.92 °C at 760 mmHg
• PKA: 8.71±0.60(Predicted)
• Flash Point: 195.06 °C
• PSA: 55.84000
• Density: 1.272 g/cm³
• LogP: 1.94470
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 321.13763628
• Heavy Atom Count: 23
• Complexity: 464

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C2CCC1C(C(C2)OC(=O)C3=CC=C(C=C3)F)C(=O)OC
• Isomeric SMILES: CN1[C@H]2CC[C@@H]1[C@H]([C@H](C2)OC(=O)C3=CC=C(C=C3)F)C(=O)OC
• Uses: A related compound of Cocaine (C633500), as substrate and inhibitor of plasma butyrylcholinesterase. Controlled substance.

Technology Process of 4'-fluorococaine

There total 1 articles about 4'-fluorococaine 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: 85.2%

4-fluorobenzoyl chloride (403-43-0) + methyl ecgonine (7143-09-1) → methyl (1R,2R,3S,5S)-3-(4'-fluorobenzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate (134507-62-3)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃; for 8h;

DOI:10.1021/ja400356g

Reference yield:

methyl (1R,2R,3S,5S)-3-(4'-fluorobenzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate (134507-62-3) → (methyl (1R,2R,3S,5S)-3-((4-fluorobenzoyl)oxy)-8-azabicyclo[3.2.1]octane-2-carboxylate) (154821-48-4)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium carbonate / benzene / 80 °C

2: zinc; formic acid / N,N-dimethyl-formamide / 20 °C

With formic acid; potassium carbonate; zinc; In N,N-dimethyl-formamide; benzene;

DOI:10.1021/ja400356g

Reference yield:

methyl (1R,2R,3S,5S)-3-(4'-fluorobenzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate (134507-62-3) + 2,2,2-Trichloroethyl chloroformate (17341-93-4) → C19H19Cl3FNO6

Guidance literature:

With potassium carbonate; In benzene; at 80 ℃;

DOI:10.1021/ja400356g

upstream raw materials:

4-fluorobenzoyl chloride

methyl ecgonine

Downstream raw materials:

(methyl (1R,2R,3S,5S)-3-((4-fluorobenzoyl)oxy)-8-azabicyclo[3.2.1]octane-2-carboxylate)

methyl (1R,2R,3S,5S)-3-(4'-fluorobenzoyloxy)-8-succinyl-8-azabicyclo[3.2.1]octane-2-carboxylate

Refernces