4-(3-cyclopentyloxy-4-methoxy-phenyl)-2-oxo-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: 4-(3-cyclopentyloxy-4-methoxy-phenyl)-2-oxo-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester
• CAS No.: 947408-11-9
• Molecular Formula: C₂₁H₂₇NO₅
• Molecular Weight: 373.449

Synonyms:4-(3-cyclopentyloxy-4-methoxy-phenyl)-2-oxo-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester

Chemical Property of 4-(3-cyclopentyloxy-4-methoxy-phenyl)-2-oxo-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester

Chemical Property:

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Technology Process of 4-(3-cyclopentyloxy-4-methoxy-phenyl)-2-oxo-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester

There total 2 articles about 4-(3-cyclopentyloxy-4-methoxy-phenyl)-2-oxo-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl 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: 71.0%

4-bromo-2-oxo-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester (947407-87-6) + 4-bromo-2-cyclopentyloxyanisole (138509-45-2) → 4-(3-cyclopentyloxy-4-methoxy-phenyl)-2-oxo-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester (947408-11-9)

Guidance literature:

4-bromo-2-cyclopentyloxyanisole; With tert.-butyl lithium; In tetrahydrofuran;

With zinc dibromide; In tetrahydrofuran;

4-bromo-2-oxo-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In N,N-dimethyl acetamide; Further stages.;

DOI:10.1055/s-2007-982553

Reference yield:

2,4-dioxo-pyrrolidine-1-carboxylic acid tert-butyl ester → 4-(3-cyclopentyloxy-4-methoxy-phenyl)-2-oxo-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester (947408-11-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 50 percent / oxalyl bromide; DMF / CH₂Cl₂ / 0 - 20 °C

2.1: tBuLi / tetrahydrofuran

2.2: ZnBr₂ / tetrahydrofuran

2.3: 71 percent / Pd₂(dibenzylideneacetone)3; 2-dicyclohexylphosphino-2'',6''-diisopropoxy-1,1''-biphenyl / N,N-dimethyl-acetamide

With Oxalyl bromide; tert.-butyl lithium; N,N-dimethyl-formamide; In tetrahydrofuran; dichloromethane; 2.3: Negishi cross-coupling reaction;

DOI:10.1055/s-2007-982553

Reference yield: 95.0%

4-(3-cyclopentyloxy-4-methoxy-phenyl)-2-oxo-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester (947408-11-9) → 4-(3-cyclopentyloxy-4-methoxy-phenyl)-1,5-dihydro-pyrrol-2-one

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1055/s-2007-982553

upstream raw materials:

4-bromo-2-oxo-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester

4-bromo-2-cyclopentyloxyanisole

Downstream raw materials:

Rolipram

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