tert-butyl-3-(4-fluorophenyl)azetidine-1-carboxylate

Base Information

• Chemical Name: tert-butyl-3-(4-fluorophenyl)azetidine-1-carboxylate
• CAS No.: 1044507-64-3
• Molecular Formula: C₁₄H₁₈FNO₂
• Molecular Weight: 251.301
• Mol file: 1044507-64-3.mol

Synonyms:tert-butyl-3-(4-fluorophenyl)azetidine-1-carboxylate

Chemical Property of tert-butyl-3-(4-fluorophenyl)azetidine-1-carboxylate

Chemical Property:

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl-3-(4-fluorophenyl)azetidine-1-carboxylate

There total 5 articles about tert-butyl-3-(4-fluorophenyl)azetidine-1-carboxylate 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: 84.0%

4-fluoroboronic acid (1765-93-1) + tert-butyl-3-iodoazetidine-1-carboxylate (254454-54-1) → tert-butyl-3-(4-fluorophenyl)azetidine-1-carboxylate (1044507-64-3)

Guidance literature:

With nickel(II) iodide; trans-2-aminocyclohexanol hydrochloride; sodium hexamethyldisilazane; In tetrahydrofuran; isopropyl alcohol; at 20 - 80 ℃; for 0.5h; Inert atmosphere; Microwave irradiation;

DOI:10.1021/jacs.0c05131

Reference yield: 74.0%

4-flourophenylmagnesium bromide (352-13-6) + tert-butyl-3-iodoazetidine-1-carboxylate (254454-54-1) → tert-butyl-3-(4-fluorophenyl)azetidine-1-carboxylate (1044507-64-3)

Guidance literature:

With (1R,2R)-bis(dimethylamino)cyclohexane; iron(II) chloride; In tetrahydrofuran; at 0 - 20 ℃; for 2h; Reagent/catalyst; Inert atmosphere;

DOI:10.1021/ol503043r

Reference yield: 63.0%

C16H25BFO2(1-)*Li(1+) + tert-butyl-3-iodoazetidine-1-carboxylate (254454-54-1) → tert-butyl-3-(4-fluorophenyl)azetidine-1-carboxylate (1044507-64-3)

Guidance literature:

With tetrakis(actonitrile)copper(I) hexafluorophosphate; 2,2,6,6-tetramethylheptane-3,5-dione; trimethylsilyl(cumyl) peroxide; triethylamine; In tetrahydrofuran; dimethyl sulfoxide; at 20 ℃; for 1h; Sealed tube; Inert atmosphere;

DOI:10.1021/jacs.1c12649

upstream raw materials:

4-fluoroboronic acid

tert-butyl-3-iodoazetidine-1-carboxylate

4-flourophenylmagnesium bromide

tert-butyl 3-hydroxyazetidine-1-carboxylate

Downstream raw materials:

3-(4-fluorophenyl)azetidine

Refernces

• 1、 Roagna, Giulia,Ascough, David M. H.,Ibba, Francesco,Vicini, Anna Chiara,Fontana, Alberto,Christensen, Kirsten E.,Peschiulli, Aldo,Oehlrich, Daniel,Misale, Antonio,Trabanco, Andrés A.,Paton, Robert S.,Pupo, Gabriele,Gouverneur, Véronique. "Hydrogen Bonding Phase-Transfer Catalysis with Ionic Reactants: Enantioselective Synthesis of γ-Fluoroamines". supporting information. p. 14045 - 14051. Retrieved 2020/09/16.
• 2、 Duncton, Matthew A. J.,Estiarte, M. Angels,Tan, Darlene,Kaub, Carl,O'Mahony, Donogh J. R.,Johnson, Russell J.,Cox, Matthew,Edwards, William T.,Wan, Min,Kincaid, John,Kelly, Michael G.. "Preparation of aryloxetanes and arylazetidines by use of an alkyl-aryl suzuki coupling". experimental part. p. 3259 - 3262. Retrieved 2009/05/07.