1-[2-(3,4-dimethoxyphenyl)ethyl]-2,5-dioxo-1,2,3,4,5,6-hexahydroindole-3a-carboxylic acid methyl ester

Base Information

• Chemical Name: 1-[2-(3,4-dimethoxyphenyl)ethyl]-2,5-dioxo-1,2,3,4,5,6-hexahydroindole-3a-carboxylic acid methyl ester
• CAS No.: 880169-65-3
• Molecular Formula: C₂₀H₂₃NO₆
• Molecular Weight: 373.406

Synonyms:1-[2-(3,4-dimethoxyphenyl)ethyl]-2,5-dioxo-1,2,3,4,5,6-hexahydroindole-3a-carboxylic acid methyl ester

Chemical Property of 1-[2-(3,4-dimethoxyphenyl)ethyl]-2,5-dioxo-1,2,3,4,5,6-hexahydroindole-3a-carboxylic acid methyl ester

Chemical Property:

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Technology Process of 1-[2-(3,4-dimethoxyphenyl)ethyl]-2,5-dioxo-1,2,3,4,5,6-hexahydroindole-3a-carboxylic acid methyl ester

There total 4 articles about 1-[2-(3,4-dimethoxyphenyl)ethyl]-2,5-dioxo-1,2,3,4,5,6-hexahydroindole-3a-carboxylic acid methyl 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: 93.0%

5-[2-(3,4-dimethoxyphenyl)ethyl]-2,2-dimethyl-6-oxo-3a,5,6,7,8,8a-hexahydro-[1,3]dioxolo[4,5-f]indole-7a-carboxylic acid methyl ester → 1-[2-(3,4-dimethoxyphenyl)ethyl]-2,5-dioxo-1,2,3,4,5,6-hexahydroindole-3a-carboxylic acid methyl ester (880169-65-3)

Guidance literature:

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

DOI:10.1021/ol0527330 DOI:10.1021/jo061269p

Reference yield:

2,2-dimethyl-6-oxo-3a,5,6,7,8,8a-hexahydro-[1,3]dioxolo[4,5-f]indole-7a-carboxylic acid methyl ester → 1-[2-(3,4-dimethoxyphenyl)ethyl]-2,5-dioxo-1,2,3,4,5,6-hexahydroindole-3a-carboxylic acid methyl ester (880169-65-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaH / dimethylformamide / 1 h / 0 °C

1.2: 80 percent / dimethylformamide / 20 °C

2.1: 93 percent / TFA / CH₂Cl₂ / 0.5 h / 20 °C

With sodium hydride; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo061269p

Reference yield:

2,2-dimethyl-6-oxo-6,7,8,8a-tetrahydro-3aH-[1,3]dioxolo[4,5-f]indole-5,7a-dicarboxylic acid 5-tert-butyl ester 7a-methyl ester → 1-[2-(3,4-dimethoxyphenyl)ethyl]-2,5-dioxo-1,2,3,4,5,6-hexahydroindole-3a-carboxylic acid methyl ester (880169-65-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 84 percent / Mg(ClO₄)2 / acetonitrile / 12 h / 20 °C

2.1: NaH / dimethylformamide / 1 h / 0 °C

2.2: 80 percent / dimethylformamide / 20 °C

3.1: 93 percent / TFA / CH₂Cl₂ / 0.5 h / 20 °C

With magnesium(II) perchlorate; sodium hydride; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo061269p

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