Trans-1-Benzyl-Azetidine-2,4-Dicarboxylic Acid Dimethyl Ester

Base Information

• Chemical Name: Trans-1-Benzyl-Azetidine-2,4-Dicarboxylic Acid Dimethyl Ester
• CAS No.: 121049-91-0
• Molecular Formula: C₁₄H₁₇NO₄
• Molecular Weight: 263.293
• Mol file: 121049-91-0.mol

Synonyms:

Chemical Property of Trans-1-Benzyl-Azetidine-2,4-Dicarboxylic Acid Dimethyl Ester

Chemical Property:

Purity/Quality:

99%min. ^*data from raw suppliers

trans-1-Benzyl-azetidine-2,4-dicarboxylicaciddimethylester 90%+ ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Trans-1-Benzyl-Azetidine-2,4-Dicarboxylic Acid Dimethyl Ester

There total 2 articles about Trans-1-Benzyl-Azetidine-2,4-Dicarboxylic Acid Dimethyl Ester 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: 48.0%

dimethyl 2,4-dibromopentanedioate (31358-13-1,31448-67-6,149198-10-7,869-09-0) + benzylamine (100-46-9) → cis-1-benzylazetidine-2,4-dicarboxylic acid dimethyl ester (121049-90-9) + trans-1-benzylazetidine-2,4-dicarboxylic acid dimethyl ester (121049-90-9,121049-91-0,127310-43-4)

Guidance literature:

In N,N-dimethyl-formamide; at 80 ℃; for 4h;

DOI:10.1016/j.bmc.2005.09.045

Reference yield:

α,α'-dibromoglutaric acid (3479-80-9) → trans-1-benzylazetidine-2,4-dicarboxylic acid dimethyl ester (121049-90-9,121049-91-0,127310-43-4)

Guidance literature:

Multi-step reaction with 2 steps

1: TsOH*H₂O / benzene / Heating

2: 36 percent / dimethylformamide / 80 °C

With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; benzene;

DOI:10.1021/jm00168a007

Reference yield:

trans-1-benzylazetidine-2,4-dicarboxylic acid dimethyl ester (121049-90-9,121049-91-0,127310-43-4) → (2S,4S)-Azetidine-2,4-dicarboxylic acid bis-[(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl] ester

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) CH₃Li / 1.) THF, 0 deg C, 25 min, 2.) THF, 2 h

2: 89 percent / H₂ / 20percent Pd(OH)2/C / ethyl acetate / 750.06 Torr / Ambient temperature

With methyllithium; hydrogen; palladium dihydroxide; In ethyl acetate;

DOI:10.1021/jm00070a016

upstream raw materials:

dimethyl 2,4-dibromopentanedioate

benzylamine

α,α'-dibromoglutaric acid

Downstream raw materials:

(2S,4S)-azetidine-2,4-dicarboxylic acid

(2R,4R)-azetidine-2,4-dicarboxylic acid

Refernces

• 1、 Kozikowski, Alan P.,Tueckmantel, Werner,Reynolds, Ian J.,Wroblewski, Jarda T.. "Synthesis and Bioactivity of a New Class of Rigid Glutamate Analogues. Modulators of the N-Methyl-D-aspartate Receptor". . p. 1561 - 1571. Retrieved 2007/10/02.