(+)-benzyl 2-methyl-1,2,3,4-tetrahydroquinoline-3-carboxylate

Base Information

• Chemical Name: (+)-benzyl 2-methyl-1,2,3,4-tetrahydroquinoline-3-carboxylate
• CAS No.: 1535966-34-7
• Molecular Formula: C₁₈H₁₉NO₂
• Molecular Weight: 281.354
• Mol file: 1535966-34-7.mol

Synonyms:(+)-benzyl 2-methyl-1,2,3,4-tetrahydroquinoline-3-carboxylate

Chemical Property of (+)-benzyl 2-methyl-1,2,3,4-tetrahydroquinoline-3-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

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• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-benzyl 2-methyl-1,2,3,4-tetrahydroquinoline-3-carboxylate

There total 3 articles about (+)-benzyl 2-methyl-1,2,3,4-tetrahydroquinoline-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:

benzyl 2-methylquinoline-3-carboxylate → (+)-benzyl 2-methyl-1,2,3,4-tetrahydroquinoline-3-carboxylate (1535966-34-7) + C18H19NO2

Guidance literature:

With bis(1,5-cyclooctadiene)diiridium(I) dichloride; C₄₂H₄₀O₆P₂; hydrogen; 3-bromo-1-chloro-5,5-dimethylhydantoin; In benzene; at 20 - 60 ℃; for 26.1667h; under 5171.62 Torr; Overall yield = 87 %; Overall yield = 50 mg; enantioselective reaction; Glovebox;

DOI:10.1055/s-0033-1339849

Reference yield:

2-methyl-3-carbethoxyquinoline (15785-08-7) → (+)-benzyl 2-methyl-1,2,3,4-tetrahydroquinoline-3-carboxylate (1535966-34-7) + C18H19NO2

Guidance literature:

Multi-step reaction with 3 steps

1.1: potassium hydroxide / ethanol; water / 1 h / Reflux

2.1: oxalyl dichloride / dichloromethane / 1 h / 20 °C

2.2: 20 °C

3.1: bis(1,5-cyclooctadiene)diiridium(I) dichloride; 3-bromo-1-chloro-5,5-dimethylhydantoin; C₄₂H₄₀O₆P₂; hydrogen / benzene / 26.17 h / 20 - 60 °C / 5171.62 Torr / Glovebox

With bis(1,5-cyclooctadiene)diiridium(I) dichloride; oxalyl dichloride; C₄₂H₄₀O₆P₂; hydrogen; 3-bromo-1-chloro-5,5-dimethylhydantoin; potassium hydroxide; In ethanol; dichloromethane; water; benzene;

DOI:10.1055/s-0033-1339849

Reference yield:

2-methylquinoline-3-carboxylic acid (635-79-0) → (+)-benzyl 2-methyl-1,2,3,4-tetrahydroquinoline-3-carboxylate (1535966-34-7) + C18H19NO2

Guidance literature:

Multi-step reaction with 2 steps

1.1: oxalyl dichloride / dichloromethane / 1 h / 20 °C

1.2: 20 °C

2.1: bis(1,5-cyclooctadiene)diiridium(I) dichloride; 3-bromo-1-chloro-5,5-dimethylhydantoin; C₄₂H₄₀O₆P₂; hydrogen / benzene / 26.17 h / 20 - 60 °C / 5171.62 Torr / Glovebox

With bis(1,5-cyclooctadiene)diiridium(I) dichloride; oxalyl dichloride; C₄₂H₄₀O₆P₂; hydrogen; 3-bromo-1-chloro-5,5-dimethylhydantoin; In dichloromethane; benzene;

DOI:10.1055/s-0033-1339849

upstream raw materials:

2-methyl-3-carbethoxyquinoline

2-methylquinoline-3-carboxylic acid

Refernces