methyl (1R)-1-[2-(3-isopropyl-1-methyl-2-{[(trifluoromethyl)sulfonyl]oxy}cyclopent-2-en-1-yl)ethyl]cyclohexa-2,5-diene-1-carboxylate

Base Information

• Chemical Name: methyl (1R)-1-[2-(3-isopropyl-1-methyl-2-{[(trifluoromethyl)sulfonyl]oxy}cyclopent-2-en-1-yl)ethyl]cyclohexa-2,5-diene-1-carboxylate
• CAS No.: 868615-30-9
• Molecular Formula: C₂₀H₂₇F₃O₅S
• Molecular Weight: 436.493

Synonyms:methyl (1R)-1-[2-(3-isopropyl-1-methyl-2-{[(trifluoromethyl)sulfonyl]oxy}cyclopent-2-en-1-yl)ethyl]cyclohexa-2,5-diene-1-carboxylate

Chemical Property of methyl (1R)-1-[2-(3-isopropyl-1-methyl-2-{[(trifluoromethyl)sulfonyl]oxy}cyclopent-2-en-1-yl)ethyl]cyclohexa-2,5-diene-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of methyl (1R)-1-[2-(3-isopropyl-1-methyl-2-{[(trifluoromethyl)sulfonyl]oxy}cyclopent-2-en-1-yl)ethyl]cyclohexa-2,5-diene-1-carboxylate

There total 14 articles about methyl (1R)-1-[2-(3-isopropyl-1-methyl-2-{[(trifluoromethyl)sulfonyl]oxy}cyclopent-2-en-1-yl)ethyl]cyclohexa-2,5-diene-1-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: 71.0%

methyl (1R)-1-[2-(3-isopropyl-1-methyl-2-oxocyclopentyl)ethyl]cyclohexa-2,5-diene-1-carboxylate (868615-37-6) + trifluoromethylsulfonic anhydride (358-23-6) → methyl (1R)-1-[2-(3-isopropyl-1-methyl-2-{[(trifluoromethyl)sulfonyl]oxy}cyclopent-2-en-1-yl)ethyl]cyclohexa-2,5-diene-1-carboxylate (868615-30-9)

Guidance literature:

With 2,6-di-tert-butyl-pyridine; In 1,2-dichloro-ethane; at 90 ℃; for 6h;

DOI:10.1002/ejoc.200600429

Reference yield:

(2R)-2-(2-iodoethyl)-5-isopropyl-2-methylcylopentanone (868615-35-4) → methyl (1R)-1-[2-(3-isopropyl-1-methyl-2-{[(trifluoromethyl)sulfonyl]oxy}cyclopent-2-en-1-yl)ethyl]cyclohexa-2,5-diene-1-carboxylate (868615-30-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 70 percent / dimethylformamide / 3 h / 110 °C

2.1: 80 percent / potassium carbonate / methanol / 5 h / 20 °C

3.1: 73 percent / pyridine / 4 h / 20 °C

4.1: 65 percent / 2,6-di-tert-butylpyridine / 1,2-dichloro-ethane / 15 h / 90 °C

5.1: 70 percent / DIBAL-H / CH₂Cl₂ / 4 h / -20 °C

6.1: 70 percent / iodine; triphenylphosphane; imidazole / CH₂Cl₂ / 2 h / 20 °C

7.1: nBuLi; diisopropylamine / tetrahydrofuran / 0.25 h / -78 °C

7.2: 65 percent / DMPU / tetrahydrofuran / 1.5 h / -78 - 50 °C

8.1: 71 percent / 2,6-di-tert-butylpyridine / 1,2-dichloro-ethane / 6 h / 90 °C

With 1H-imidazole; n-butyllithium; 2,6-di-tert-butyl-pyridine; iodine; diisobutylaluminium hydride; potassium carbonate; diisopropylamine; triphenylphosphine; In tetrahydrofuran; pyridine; methanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.200600429

Reference yield:

(1R)-3-(3-isopropyl-1-methyl-2-oxocyclopentyl)propanoic acid (868615-50-3) → methyl (1R)-1-[2-(3-isopropyl-1-methyl-2-{[(trifluoromethyl)sulfonyl]oxy}cyclopent-2-en-1-yl)ethyl]cyclohexa-2,5-diene-1-carboxylate (868615-30-9)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 65 percent / Pb(OAc)4; I₂ / CCl₄ / 1 h / 80 °C / Irradiation

2.1: 70 percent / dimethylformamide / 3 h / 110 °C

3.1: 80 percent / potassium carbonate / methanol / 5 h / 20 °C

4.1: 73 percent / pyridine / 4 h / 20 °C

5.1: 65 percent / 2,6-di-tert-butylpyridine / 1,2-dichloro-ethane / 15 h / 90 °C

6.1: 70 percent / DIBAL-H / CH₂Cl₂ / 4 h / -20 °C

7.1: 70 percent / iodine; triphenylphosphane; imidazole / CH₂Cl₂ / 2 h / 20 °C

8.1: nBuLi; diisopropylamine / tetrahydrofuran / 0.25 h / -78 °C

8.2: 65 percent / DMPU / tetrahydrofuran / 1.5 h / -78 - 50 °C

9.1: 71 percent / 2,6-di-tert-butylpyridine / 1,2-dichloro-ethane / 6 h / 90 °C

With 1H-imidazole; lead(IV) acetate; n-butyllithium; 2,6-di-tert-butyl-pyridine; iodine; diisobutylaluminium hydride; potassium carbonate; diisopropylamine; triphenylphosphine; In tetrahydrofuran; pyridine; methanol; tetrachloromethane; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.200600429

upstream raw materials:

methyl (1R)-1-[2-(3-isopropyl-1-methyl-2-oxocyclopentyl)ethyl]cyclohexa-2,5-diene-1-carboxylate

trifluoromethylsulfonic anhydride

(2R)-2-(2-iodoethyl)-5-isopropyl-2-methylcylopentanone

methyl (1R)-3-(3-isopropyl-1-methyl-2-oxocyclopentyl)propanoate

Downstream raw materials:

methyl (1R)-1-[2-(3-isopropyl-1-methyl-2-{[(trifluoromethyl)sulfonyl]oxy}cyclopent-2-en-1-yl)ethyl]-4-oxocyclohexa-2,5-diene-1-carboxylate

(5S)-5-{2-[1-(hydroxymethyl)cyclohexa-2,5-dien-1-yl]ethyl}-2-isopropyl-5-methylcyclopent-1-en-1-yl trifluoromethanesulfonate

(1S)-{1-[2-(3-isopropyl-1-methyl-2-{[(trifluoromethyl)sulfonyl]oxy}cyclopent-2-en-1-yl)ethyl]cyclohexa-2,5-dien-1-yl}methyl 2,2-dimethylpropanoate

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