2H-Isoindole-1-carboxylic acid, 4,5,6,7-tetrahydro-3-[[5-oxo-1-(phenylmethyl)-2-pyrrolidinylidene]methyl] -, methyl ester, (Z)-

Base Information

• Chemical Name: 2H-Isoindole-1-carboxylic acid, 4,5,6,7-tetrahydro-3-[[5-oxo-1-(phenylmethyl)-2-pyrrolidinylidene]methyl] -, methyl ester, (Z)-
• CAS No.: 145100-14-7
• Molecular Formula: C₂₂H₂₄N₂O₃
• Molecular Weight: 364.444
• Mol file: 145100-14-7.mol

Synonyms:

Chemical Property of 2H-Isoindole-1-carboxylic acid, 4,5,6,7-tetrahydro-3-[[5-oxo-1-(phenylmethyl)-2-pyrrolidinylidene]methyl] -, methyl ester, (Z)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2H-Isoindole-1-carboxylic acid, 4,5,6,7-tetrahydro-3-[[5-oxo-1-(phenylmethyl)-2-pyrrolidinylidene]methyl] -, methyl ester, (Z)-

There total 3 articles about 2H-Isoindole-1-carboxylic acid, 4,5,6,7-tetrahydro-3-[[5-oxo-1-(phenylmethyl)-2-pyrrolidinylidene]methyl] -, methyl ester, (Z)- 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: 42.0%

3-(4-Benzylcarbamoyl-but-1-ynyl)-4,5,6,7-tetrahydro-2H-isoindole-1-carboxylic acid methyl ester (145100-08-9) → 3-[1-Benzyl-5-oxo-pyrrolidin-(2Z)-ylidenemethyl]-4,5,6,7-tetrahydro-2H-isoindole-1-carboxylic acid methyl ester (145100-14-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; Heating;

DOI:10.1016/S0040-4039(00)60941-3

Reference yield:

methyl 4,5,6,7-tetrahydro-2H-isoindole-1-carboxylate (60652-00-8) → 3-[1-Benzyl-5-oxo-pyrrolidin-(2Z)-ylidenemethyl]-4,5,6,7-tetrahydro-2H-isoindole-1-carboxylic acid methyl ester (145100-14-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 89 percent / N-iodosuccinimide

2: 93 percent / Et₃N / Pd(Ph₃P)4, CuI / dimethylformamide / 22 °C

3: 42 percent / n-Bu₄NF / tetrahydrofuran / Heating

With N-iodo-succinimide; tetrabutyl ammonium fluoride; triethylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)60941-3

Reference yield:

1-carbomethoxy-3-iodo-4,5,6,7-tetrahydro-2H-isoindole (145100-02-3) → 3-[1-Benzyl-5-oxo-pyrrolidin-(2Z)-ylidenemethyl]-4,5,6,7-tetrahydro-2H-isoindole-1-carboxylic acid methyl ester (145100-14-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / Et₃N / Pd(Ph₃P)4, CuI / dimethylformamide / 22 °C

2: 42 percent / n-Bu₄NF / tetrahydrofuran / Heating

With tetrabutyl ammonium fluoride; triethylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)60941-3

upstream raw materials:

3-(4-Benzylcarbamoyl-but-1-ynyl)-4,5,6,7-tetrahydro-2H-isoindole-1-carboxylic acid methyl ester

methyl 4,5,6,7-tetrahydro-2H-isoindole-1-carboxylate

1-carbomethoxy-3-iodo-4,5,6,7-tetrahydro-2H-isoindole