3,4-dihydro-6,7-dimethoxy-1-(3,4-dimethoxyphenyl)methyl-2(1H)-isoquinolinecarboxylic acid 1,1-dimethylethyl ester

Base Information

• Chemical Name: 3,4-dihydro-6,7-dimethoxy-1-(3,4-dimethoxyphenyl)methyl-2(1H)-isoquinolinecarboxylic acid 1,1-dimethylethyl ester
• CAS No.: 140367-63-1
• Molecular Formula: C₂₅H₃₃NO₆
• Molecular Weight: 443.54
• Mol file: 140367-63-1.mol

Synonyms:3,4-dihydro-6,7-dimethoxy-1-(3,4-dimethoxyphenyl)methyl-2(1H)-isoquinolinecarboxylic acid 1,1-dimethylethyl ester

Chemical Property of 3,4-dihydro-6,7-dimethoxy-1-(3,4-dimethoxyphenyl)methyl-2(1H)-isoquinolinecarboxylic acid 1,1-dimethylethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,4-dihydro-6,7-dimethoxy-1-(3,4-dimethoxyphenyl)methyl-2(1H)-isoquinolinecarboxylic acid 1,1-dimethylethyl ester

There total 9 articles about 3,4-dihydro-6,7-dimethoxy-1-(3,4-dimethoxyphenyl)methyl-2(1H)-isoquinolinecarboxylic acid 1,1-dimethylethyl 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: 75.0%

3,4-dihydro-6,7-dimethoxy-2(1H)-isoquinolinecarboxylic acid 1,1-dimethylethyl ester (127119-08-8) + 4-chloromethyl-1,2-dimethoxy-benzene (7306-46-9) → 3,4-dihydro-6,7-dimethoxy-1-(3,4-dimethoxyphenyl)methyl-2(1H)-isoquinolinecarboxylic acid 1,1-dimethylethyl ester (140367-63-1)

Guidance literature:

3,4-dihydro-6,7-dimethoxy-2(1H)-isoquinolinecarboxylic acid 1,1-dimethylethyl ester; With n-butyllithium; In tetrahydrofuran; hexane; at -50 ℃; for 0.0666667h; Inert atmosphere;

4-chloromethyl-1,2-dimethoxy-benzene; In tetrahydrofuran; hexane; at -50 - 20 ℃; for 16h; Inert atmosphere;

DOI:10.1002/chem.201301096

Reference yield: 50.0%

di-tert-butyl dicarbonate (24424-99-5) + 1-(2-azidoethyl)-2-(3,4-dimethoxyphenethyl)-4,5-dimethoxybenzene → 3,4-dihydro-6,7-dimethoxy-1-(3,4-dimethoxyphenyl)methyl-2(1H)-isoquinolinecarboxylic acid 1,1-dimethylethyl ester (140367-63-1)

Guidance literature:

With iron(II)-tetra-tert-butylphthalocyaninato complex with an axial pyridine ligand; In toluene; at 130 ℃; Schlenk technique; Inert atmosphere;

DOI:10.1039/d1cc04573c

Reference yield:

1-(2-chloroethyl)-2-(3,4-dimethoxyphenethyl)-4,5-dimethoxybenzene → 3,4-dihydro-6,7-dimethoxy-1-(3,4-dimethoxyphenyl)methyl-2(1H)-isoquinolinecarboxylic acid 1,1-dimethylethyl ester (140367-63-1)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium azide / N,N-dimethyl-formamide / 80 °C

2: iron(II)-tetra-tert-butylphthalocyaninato complex with an axial pyridine ligand / toluene / 130 °C / Schlenk technique; Inert atmosphere

With sodium azide; In N,N-dimethyl-formamide; toluene;

DOI:10.1039/d1cc04573c

upstream raw materials:

4-bromomethyl-1,2-dimethoxybenzene

3,4-dihydro-6,7-dimethoxy-2(1H)-isoquinolinecarboxylic acid 1,1-dimethylethyl ester

6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

di-tert-butyl dicarbonate

Downstream raw materials:

laudanosine

Tetrahydropapaverine

Refernces

• 1、 Li, Xiabing,Leonori, Daniele,Sheikh, Nadeem S.,Coldham, Iain. "Synthesis of 1-substituted tetrahydroisoquinolines by lithiation and electrophilic quenching guided by in situ IR and NMR spectroscopy and application to the synthesis of salsolidine, carnegine and laudanosine". supporting information. p. 7724 - 7730. Retrieved 2013/07/19.