4-(4-tert-butyl-phenyl)-2,3-dihydro-pyrrole-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Base Information

• Chemical Name: 4-(4-tert-butyl-phenyl)-2,3-dihydro-pyrrole-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester
• CAS No.: 1027152-54-0
• Molecular Formula: C₂₁H₂₉NO₄
• Molecular Weight: 359.466
• Mol file: 1027152-54-0.mol

Synonyms:4-(4-tert-butyl-phenyl)-2,3-dihydro-pyrrole-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Chemical Property of 4-(4-tert-butyl-phenyl)-2,3-dihydro-pyrrole-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-(4-tert-butyl-phenyl)-2,3-dihydro-pyrrole-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

There total 3 articles about 4-(4-tert-butyl-phenyl)-2,3-dihydro-pyrrole-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl 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:

p-tert-butylphenylboronic acid (123324-71-0) + 1-tert-butyl 2-methyl (2S)-4-(trifluoromethanesulfonyloxy)-2,3-dihydropyrrole-1,2-dicarboxylate (284047-10-5) → 4-(4-tert-butyl-phenyl)-2,3-dihydro-pyrrole-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (1027152-54-0)

Guidance literature:

With trans benzyl(chloro)bis(triphenylphosphine)palladium(II); sodium carbonate; lithium chloride; In 1,2-dimethoxyethane; at 86 ℃;

DOI:10.1248/cpb.48.740

Reference yield:

(S)-1-tert-butyl 2-methyl 4-oxopyrrolidine-1,2-dicarboxylate (102195-80-2) → 4-(4-tert-butyl-phenyl)-2,3-dihydro-pyrrole-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (1027152-54-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: LiN[Si(CH₃)3]2 / tetrahydrofuran / -78 °C

1.2: 30 percent / tetrahydrofuran / -78 - 20 °C

2.1: (PhCH₂)(Cl)Pd(PPh₃)2; LiCl; aq. Na₂CO₃ / 1,2-dimethoxy-ethane / 86 °C

With trans benzyl(chloro)bis(triphenylphosphine)palladium(II); sodium carbonate; lithium chloride; lithium hexamethyldisilazane; In tetrahydrofuran; 1,2-dimethoxyethane; 1.1: Enolization / 1.2: Triflation / 2.1: Arylation;

DOI:10.1248/cpb.48.740

Reference yield:

1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate (74844-91-0) → 4-(4-tert-butyl-phenyl)-2,3-dihydro-pyrrole-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (1027152-54-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 100 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

2.1: LiN[Si(CH₃)3]2 / tetrahydrofuran / -78 °C

2.2: 30 percent / tetrahydrofuran / -78 - 20 °C

3.1: (PhCH₂)(Cl)Pd(PPh₃)2; LiCl; aq. Na₂CO₃ / 1,2-dimethoxy-ethane / 86 °C

With oxalyl dichloride; trans benzyl(chloro)bis(triphenylphosphine)palladium(II); sodium carbonate; dimethyl sulfoxide; triethylamine; lithium chloride; lithium hexamethyldisilazane; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; 1.1: Oxidation / 2.1: Enolization / 2.2: Triflation / 3.1: Arylation;

DOI:10.1248/cpb.48.740

upstream raw materials:

p-tert-butylphenylboronic acid

1-tert-butyl 2-methyl (2S)-4-(trifluoromethanesulfonyloxy)-2,3-dihydropyrrole-1,2-dicarboxylate

1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate

(S)-1-tert-butyl 2-methyl 4-oxopyrrolidine-1,2-dicarboxylate

Downstream raw materials:

4-(4-tert-butyl-phenyl)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester

4-(4-tert-butyl-phenyl)-2-(1-methoxycarbonyl-3-methylsulfanyl-propylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

(R)-4-{(E)-3-[(2S,4R)-4-(4-tert-Butyl-phenyl)-2-((S)-1-methoxycarbonyl-3-methylsulfanyl-propylcarbamoyl)-pyrrolidin-1-yl]-propenyl}-2,2-dimethyl-thiazolidine-3-carboxylic acid tert-butyl ester

C₃₃H₅₁N₃O₇S₃