1-[2-(3,4-Dimethoxy-phenyl)-ethyl]-9b-hydroxy-2,5-dioxo-1,2,3,4,5,9b-hexahydro-benzo[g]indole-3a-carboxylic acid methyl ester

Base Information

Chemical Name:1-[2-(3,4-Dimethoxy-phenyl)-ethyl]-9b-hydroxy-2,5-dioxo-1,2,3,4,5,9b-hexahydro-benzo[g]indole-3a-carboxylic acid methyl ester
CAS No.:179945-83-6
Molecular Formula:C₂₄H₂₅NO₇
Molecular Weight:439.465
Hs Code.:

Synonyms:1-[2-(3,4-Dimethoxy-phenyl)-ethyl]-9b-hydroxy-2,5-dioxo-1,2,3,4,5,9b-hexahydro-benzo[g]indole-3a-carboxylic acid methyl ester

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Chemical Property of 1-[2-(3,4-Dimethoxy-phenyl)-ethyl]-9b-hydroxy-2,5-dioxo-1,2,3,4,5,9b-hexahydro-benzo[g]indole-3a-carboxylic acid methyl ester

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Technology Process of 1-[2-(3,4-Dimethoxy-phenyl)-ethyl]-9b-hydroxy-2,5-dioxo-1,2,3,4,5,9b-hexahydro-benzo[g]indole-3a-carboxylic acid methyl ester

There total 5 articles about 1-[2-(3,4-Dimethoxy-phenyl)-ethyl]-9b-hydroxy-2,5-dioxo-1,2,3,4,5,9b-hexahydro-benzo[g]indole-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: 47.0%

: 179945-79-0
4-[[2-(3,4-Dimethoxy-phenyl)-ethyl]-(2-ethanesulfinylmethyl-benzoyl)-amino]-2-methylene-4-oxo-butyric acid methyl ester

: 179945-83-6
1-[2-(3,4-Dimethoxy-phenyl)-ethyl]-9b-hydroxy-2,5-dioxo-1,2,3,4,5,9b-hexahydro-benzo[g]indole-3a-carboxylic acid methyl ester

: 179945-82-5
1-[2-(3,4-Dimethoxy-phenyl)-ethyl]-9b-ethylsulfanyl-2,5-dioxo-1,2,3,4,5,9b-hexahydro-benzo[g]indole-3a-carboxylic acid methyl ester

Guidance literature:: With acetic anhydride; toluene-4-sulfonic acid; In toluene;
DOI:10.1021/jo960818w

Reference yield:

: 79313-52-3
2-Ethylsulfanylmethyl-benzoic acid

: 179945-83-6
1-[2-(3,4-Dimethoxy-phenyl)-ethyl]-9b-hydroxy-2,5-dioxo-1,2,3,4,5,9b-hexahydro-benzo[g]indole-3a-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: SOCl₂ / benzene / 1 h / Ambient temperature

2: 7.8 g / CH₂Cl₂ / 2 h / Ambient temperature

3: 83 percent / 4A MS / CH₂Cl₂ / 24 h / Ambient temperature

4: 93 percent / NaIO₄

5: 23 percent / p-TsOH, Ac₂O / xylene / 0.17 h / Heating

With sodium periodate; thionyl chloride; acetic anhydride; toluene-4-sulfonic acid; In dichloromethane; xylene; benzene;
DOI:10.1021/jo9716183

Reference yield:

: 2-Ethylsulfanylmethyl-benzoyl chloride

: 179945-83-6
1-[2-(3,4-Dimethoxy-phenyl)-ethyl]-9b-hydroxy-2,5-dioxo-1,2,3,4,5,9b-hexahydro-benzo[g]indole-3a-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 7.8 g / CH₂Cl₂ / 2 h / Ambient temperature

2: 83 percent / 4A MS / CH₂Cl₂ / 24 h / Ambient temperature

3: 93 percent / NaIO₄

4: 23 percent / p-TsOH, Ac₂O / xylene / 0.17 h / Heating

With sodium periodate; acetic anhydride; toluene-4-sulfonic acid; In dichloromethane; xylene;
DOI:10.1021/jo9716183