(3aS,7aS)-2-[2-(3,4-dimethoxyphenyl)ethyl]-1,3-dioxo-octahydro-isoindole-3a-carboxylic acid methyl ester

Base Information

Chemical Name:(3aS,7aS)-2-[2-(3,4-dimethoxyphenyl)ethyl]-1,3-dioxo-octahydro-isoindole-3a-carboxylic acid methyl ester
CAS No.:501085-21-8
Molecular Formula:C₂₀H₂₅NO₆
Molecular Weight:375.422
Hs Code.:

Synonyms:(3aS,7aS)-2-[2-(3,4-dimethoxyphenyl)ethyl]-1,3-dioxo-octahydro-isoindole-3a-carboxylic acid methyl ester

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Chemical Property of (3aS,7aS)-2-[2-(3,4-dimethoxyphenyl)ethyl]-1,3-dioxo-octahydro-isoindole-3a-carboxylic acid methyl ester

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Technology Process of (3aS,7aS)-2-[2-(3,4-dimethoxyphenyl)ethyl]-1,3-dioxo-octahydro-isoindole-3a-carboxylic acid methyl ester

There total 7 articles about (3aS,7aS)-2-[2-(3,4-dimethoxyphenyl)ethyl]-1,3-dioxo-octahydro-isoindole-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: 87.0%

: 17640-15-2
methyl cyanoformate

: 26478-05-7
(3aSR,7aRS)-2-[2-(3,4-dimethoxyphenyl)ethyl]-hexahydro-isoindole-1,3-dione

: 501085-21-8
(3aS,7aS)-2-[2-(3,4-dimethoxyphenyl)ethyl]-1,3-dioxo-octahydro-isoindole-3a-carboxylic acid methyl ester

Guidance literature:: (3aSR,7aRS)-2-[2-(3,4-dimethoxyphenyl)ethyl]-hexahydro-isoindole-1,3-dione; With n-butyllithium; (1S,2S)-1,2-diphenyl-N,N'-bis((R)-1-phenylethyl)ethane-1,2-diamine; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

methyl cyanoformate; In tetrahydrofuran; hexane; at -78 ℃; for 1.25h;
DOI:10.15227/orgsyn.084.0306

Reference yield: 85.7%

: 17640-15-2
methyl cyanoformate

: 26478-05-7
(3aSR,7aRS)-2-[2-(3,4-dimethoxyphenyl)ethyl]-hexahydro-isoindole-1,3-dione

: 120-20-7
2-(3,4-dimethoxyphenyl)-ethylamine

: 501085-21-8
(3aS,7aS)-2-[2-(3,4-dimethoxyphenyl)ethyl]-1,3-dioxo-octahydro-isoindole-3a-carboxylic acid methyl ester

Guidance literature:: 2-(3,4-dimethoxyphenyl)-ethylamine; With n-butyllithium; chiral PhCH(Me)NLiCH(Ph)CH(Ph)NHCH(Me)Ph; In tetrahydrofuran; at 20 ℃; for 0.5h;

(3aSR,7aRS)-2-[2-(3,4-dimethoxyphenyl)ethyl]-hexahydro-isoindole-1,3-dione; In tetrahydrofuran; at -78 ℃; for 1.5h;

methyl cyanoformate; In tetrahydrofuran; at -78 ℃; for 1h; Further stages.;
DOI:10.1021/ol027447s

Reference yield:

: 13149-00-3
1,2-cis-cyclohexanedicarboxylic anhydride

: 501085-21-8
(3aS,7aS)-2-[2-(3,4-dimethoxyphenyl)ethyl]-1,3-dioxo-octahydro-isoindole-3a-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: 87 percent / acetic acid / 18 h / Heating

2.1: chiral lithium amide base / tetrahydrofuran; hexane / 1.5 h / -78 °C

2.2: 86 percent / tetrahydrofuran; hexane / -78 °C

With chiral lithium amide base; In tetrahydrofuran; hexane; acetic acid;
DOI:10.1016/j.tet.2003.08.046