methyl 2-(2-(2,5-dimethoxy phenyl) acetyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate

Base Information

Chemical Name:methyl 2-(2-(2,5-dimethoxy phenyl) acetyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate
CAS No.:1326317-15-0
Molecular Formula:C₂₃H₂₇NO₇
Molecular Weight:429.47
Hs Code.:

Synonyms:methyl 2-(2-(2,5-dimethoxy phenyl) acetyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate

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Chemical Property of methyl 2-(2-(2,5-dimethoxy phenyl) acetyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate

Chemical Property:

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Technology Process of methyl 2-(2-(2,5-dimethoxy phenyl) acetyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate

There total 6 articles about methyl 2-(2-(2,5-dimethoxy phenyl) acetyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-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:

: 52711-92-9
2,5-dimethoxyphenylacetyl chloride

: 88932-16-5
1,2,3,4-tetrahydro-6,7-dimethoxy-3-Isoquinolinecarboxylic acid methyl ester

: 1326317-15-0
methyl 2-(2-(2,5-dimethoxy phenyl) acetyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate

Guidance literature:: With triethylamine; In dichloromethane; at 0 ℃; Reflux;
DOI:10.1016/j.tet.2012.01.005

Reference yield:

: 120-14-9
3,4-dimethoxy-benzaldehyde

: 1326317-15-0
methyl 2-(2-(2,5-dimethoxy phenyl) acetyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 0.5 h / 0 °C

1.2: 20 °C

2.1: palladium 10% on activated carbon; hydrogen / ethanol / 5 h / 20 °C

3.1: trifluoroacetic acid / dichloromethane / 4 h / 0 - 20 °C

4.1: trifluoroacetic acid / dichloromethane; water / 5.25 h / 20 °C

5.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C / Inert atmosphere

With dmap; palladium 10% on activated carbon; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In tetrahydrofuran; ethanol; dichloromethane; water; 1.1: Horner-Wadsworth-Emmons olefination / 1.2: Horner-Wadsworth-Emmons olefination / 4.1: Pictet-Spengler cyclisation;
DOI:10.1021/jm2008387

Reference yield:

: 56771-16-5,59291-28-0,78083-80-4,78392-35-5
2-amino-3-(3,4-dimethoxybenz-1-yl)propanoic acid methyl ester

: 1326317-15-0
methyl 2-(2-(2,5-dimethoxy phenyl) acetyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: trifluoroacetic acid / dichloromethane; water / 5.25 h / 20 °C

2: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C / Inert atmosphere

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In dichloromethane; water; 1: Pictet-Spengler cyclisation;
DOI:10.1021/jm2008387