(R)-1-(3,4-dimethoxyphenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

Base Information

• Chemical Name: (R)-1-(3,4-dimethoxyphenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
• CAS No.: 33770-41-1
• Molecular Formula: C₁₉H₂₃NO₄
• Molecular Weight: 329.396
• Mol file: 33770-41-1.mol

Synonyms:(R)-1-(3,4-dimethoxyphenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

Chemical Property of (R)-1-(3,4-dimethoxyphenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-1-(3,4-dimethoxyphenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

There total 8 articles about (R)-1-(3,4-dimethoxyphenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 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: 66.0%

(R)-2-((S)-2-Benzyloxymethyl-pyrrolidin-1-yl)-6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydro-isoquinoline → (R)-1-(3,4-dimethoxyphenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (33770-41-1) + (2S)-benzyloxymethyl-pyrrolidine (89597-97-7)

Guidance literature:

With boron trifluoride-tetrahydrofuran complex; for 20h; Heating;

DOI:10.1016/00404-0399(50)1358-O

Reference yield:

1-(3,4-dimethoxy-phenyl)-6,7-dimethoxy-3,4-dihydro-isoquinoline (15547-57-6) → (R)-1-(3,4-dimethoxyphenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (33770-41-1) + (S)-1-1-(3',4'-dimethoxylphenyl)-1,2,3,4-tetrahydro-6,7-dimethoxyisoquinoline (33770-43-3)

Guidance literature:

With phthalimide; chloro(1,5-cyclooctadiene)iridium(I) dimer; hydrogen; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); In methanol; toluene; at 5 ℃; for 96h; under 76000 Torr; Product distribution;

DOI:10.3987/COM-96-7635

Reference yield:

N-<2-(3,4-dimethoxyphenyl)ethyl>-3,4-dimethoxyphenylacetamide (102011-15-4) → (R)-1-(3,4-dimethoxyphenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (33770-41-1) + (S)-1-1-(3',4'-dimethoxylphenyl)-1,2,3,4-tetrahydro-6,7-dimethoxyisoquinoline (33770-43-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: trifluoromethylsulfonic anhydride / dichloromethane / -78 °C / Inert atmosphere

1.2: Inert atmosphere

2.1: formic acid; RuCl[(1R,2R)-p-TsNCH(C6H5)CH-(C6H5)NH2](η6-benzene); triethylamine / isopropyl alcohol / 16 h / 30 °C / Inert atmosphere

With formic acid; RuCl[(1R,2R)-p-TsNCH(C6H5)CH-(C6H5)NH2](η6-benzene); trifluoromethylsulfonic anhydride; triethylamine; In dichloromethane; isopropyl alcohol; 1.1: |Bischler-Napieralski Reaction / 1.2: |Bischler-Napieralski Reaction;

DOI:10.1002/ejoc.201500951

upstream raw materials:

1-(3,4-dimethoxy-phenyl)-6,7-dimethoxy-3,4-dihydro-isoquinoline

N-<2-(3,4-dimethoxyphenyl)ethyl>-3,4-dimethoxyphenylacetamide

3,4-dimethoxybenzoic acid chloride

2-(3,4-dimethoxyphenyl)-ethylamine

Downstream raw materials:

1-(3',4'-dimethoxyphenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

(S)-1-1-(3',4'-dimethoxylphenyl)-1,2,3,4-tetrahydro-6,7-dimethoxyisoquinoline

1-(3,4-dimethoxy-phenyl)-6,7-dimethoxy-3,4-dihydro-isoquinoline