(4R)-ethyl-4-(3-(cyclopentyloxy)-4-methoxyphenyl)-2-oxopyrrolidine-3-carboxylate

Base Information

• Chemical Name: (4R)-ethyl-4-(3-(cyclopentyloxy)-4-methoxyphenyl)-2-oxopyrrolidine-3-carboxylate
• CAS No.: 478919-14-1
• Molecular Formula: C₁₉H₂₅NO₅
• Molecular Weight: 347.411
• Mol file: 478919-14-1.mol

Synonyms:(4R)-ethyl-4-(3-(cyclopentyloxy)-4-methoxyphenyl)-2-oxopyrrolidine-3-carboxylate

Chemical Property of (4R)-ethyl-4-(3-(cyclopentyloxy)-4-methoxyphenyl)-2-oxopyrrolidine-3-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R)-ethyl-4-(3-(cyclopentyloxy)-4-methoxyphenyl)-2-oxopyrrolidine-3-carboxylate

There total 7 articles about (4R)-ethyl-4-(3-(cyclopentyloxy)-4-methoxyphenyl)-2-oxopyrrolidine-3-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: 96.0%

diethyl 2-((1S)-1-(3-(cyclopentyloxy)-4-methoxyphenyl)-2-nitroethyl)malonate (478919-15-2) → (4R)-ethyl-4-(3-(cyclopentyloxy)-4-methoxyphenyl)-2-oxopyrrolidine-3-carboxylate (478919-14-1)

Guidance literature:

With hydrogen; In methanol; at 20 ℃; for 12h;

DOI:10.1080/00397911.2011.580880

Reference yield: 94.0%

diethyl 2-((1R)-1-(3-(cyclopentyloxy)-4-methoxyphenyl)-2-nitroethyl)malonate (478919-13-0) → (4R)-ethyl-4-(3-(cyclopentyloxy)-4-methoxyphenyl)-2-oxopyrrolidine-3-carboxylate (478919-14-1)

Guidance literature:

With hydrogen; In ethanol; water; at 20 ℃; for 12h; under 1034.32 Torr; Autoclave;

DOI:10.1016/j.tetlet.2020.152792

Reference yield:

isovanillin (621-59-0) → (4R)-ethyl-4-(3-(cyclopentyloxy)-4-methoxyphenyl)-2-oxopyrrolidine-3-carboxylate (478919-14-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 97 percent / K₂CO₃ / dimethylformamide / 100 °C

2: 90 percent / NH₄OAc; acetic acid / 2 h / 90 °C

3: 95 percent / 1,1-bis(3aR,8aS-dihydroindeno[1,2-d]oxazol-2-yl)cyclopropane; Mg(OTf)2*4H₂O; N-methylmorpholine / 4A molecular sieves / CHCl₃ / 20 °C

4: H₂; H₂PO₄ / Raney-Ni / tetrahydrofuran / 2 h / 50 °C / 2068.65 - 2585.81 Torr

With 4-methyl-morpholine; (3aR,3a’R,8aS,8a’S)-2,2’-(cyclopropane-1,1-diyl)bis(3a,8a-dihydro-8H-indeno[1,2-d]-oxazole); ammonium acetate; hydrogen; dihydrogen phosphate; potassium carbonate; acetic acid; magnesium triflate; 4 A molecular sieve; nickel; In tetrahydrofuran; chloroform; N,N-dimethyl-formamide; 3: Michael addition;

DOI:10.1021/ja026788y

upstream raw materials:

diethyl 2-((1R)-1-(3-(cyclopentyloxy)-4-methoxyphenyl)-2-nitroethyl)malonate

isovanillin

Cyclopentyl bromide

3-cyclopentyloxy-4-methoxybenzylaldehyde

Downstream raw materials:

(R)-4-(3-cyclopentyloxy-4-methoxyphenyl)pyrrolidin-2-one