(R)-1-ethenyl-2-trifluoroacetyl-5,6,7-trimethoxy-1,2,3,4-tetrahydroisoquinoline

Base Information

• Chemical Name: (R)-1-ethenyl-2-trifluoroacetyl-5,6,7-trimethoxy-1,2,3,4-tetrahydroisoquinoline
• CAS No.: 1332523-78-0
• Molecular Formula: C₁₆H₁₈F₃NO₄
• Molecular Weight: 345.318
• Mol file: 1332523-78-0.mol

Synonyms:(R)-1-ethenyl-2-trifluoroacetyl-5,6,7-trimethoxy-1,2,3,4-tetrahydroisoquinoline

Chemical Property of (R)-1-ethenyl-2-trifluoroacetyl-5,6,7-trimethoxy-1,2,3,4-tetrahydroisoquinoline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-1-ethenyl-2-trifluoroacetyl-5,6,7-trimethoxy-1,2,3,4-tetrahydroisoquinoline

There total 10 articles about (R)-1-ethenyl-2-trifluoroacetyl-5,6,7-trimethoxy-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:

2,2,2-trifluoroethanol (75-89-8) + ethenyl (Z)-3-{3,4,5-trimethoxy-2-[2-(trifluoroacetylamino)ethyl]phenyl}prop-2-enyl carbonate (1332523-87-1) → (S)-1-ethenyl-2-trifluoroacetyl-5,6,7-trimethoxy-1,2,3,4-tetrahydroisoquinoline (1332523-74-6) + (R)-1-ethenyl-2-trifluoroacetyl-5,6,7-trimethoxy-1,2,3,4-tetrahydroisoquinoline (1332523-78-0) + 1-[(Z)-3-(2,2,2-trifluoroethoxy)prop-1-enyl]-2-[2-(trifluoroacetylamino)ethyl]-2,3,4-trimethoxybenzene (1332523-99-5)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; (S)-O,O'-(3,3'-bis(naphthalen-1-ylmethyl)-5,5',6,6'-tetramethyl-1,1'-biphenyl-2,2'-diyl)-N,N-dimethylphosphoramidite; In dichloromethane; at 20 ℃; for 2h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1016/j.tet.2011.05.125

Reference yield:

2,2,2-trifluoroethanol (75-89-8) + 2,6-dimethylphenyl (Z)-3-{3,4,5-trimethoxy-2-[2-(trifluoroacetylamino)ethyl]phenyl}prop-2-enyl carbonate (1332523-96-2) → (S)-1-ethenyl-2-trifluoroacetyl-5,6,7-trimethoxy-1,2,3,4-tetrahydroisoquinoline (1332523-74-6) + (R)-1-ethenyl-2-trifluoroacetyl-5,6,7-trimethoxy-1,2,3,4-tetrahydroisoquinoline (1332523-78-0) + 1-[(Z)-3-(2,2,2-trifluoroethoxy)prop-1-enyl]-2-[2-(trifluoroacetylamino)ethyl]-2,3,4-trimethoxybenzene (1332523-99-5)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; (S)-O,O'-(3,3'-bis(naphthalen-1-ylmethyl)-5,5',6,6'-tetramethyl-1,1'-biphenyl-2,2'-diyl)-N,N-dimethylphosphoramidite; In dichloromethane; at 20 ℃; for 2h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1016/j.tet.2011.05.125

Reference yield:

N-[2-(2,3,4-trimethoxyphenyl)ethyl]-2,2,2-trifluoroacetamide (1332523-79-1) → (S)-1-ethenyl-2-trifluoroacetyl-5,6,7-trimethoxy-1,2,3,4-tetrahydroisoquinoline (1332523-74-6) + (R)-1-ethenyl-2-trifluoroacetyl-5,6,7-trimethoxy-1,2,3,4-tetrahydroisoquinoline (1332523-78-0) + 1-[(Z)-3-(2,2,2-trifluoroethoxy)prop-1-enyl]-2-[2-(trifluoroacetylamino)ethyl]-2,3,4-trimethoxybenzene (1332523-99-5)

Guidance literature:

Multi-step reaction with 6 steps

1: N-Bromosuccinimide / tetrachloromethane / 16 h / 60 °C / Inert atmosphere

2: N-iodo-succinimide; trifluoroacetic acid / acetonitrile / 24 h / Inert atmosphere; Reflux

3: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; diethylamine / 18 h / Inert atmosphere; Reflux

4: sodium tetrahydroborate; hydrogen; nickel diacetate; ethylenediamine / ethanol / 40 h / 20 °C / 760.05 Torr

5: pyridine / dichloromethane / 3 h / 0 °C / Inert atmosphere

6: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; (S)-O,O'-(3,3'-bis(naphthalen-1-ylmethyl)-5,5',6,6'-tetramethyl-1,1'-biphenyl-2,2'-diyl)-N,N-dimethylphosphoramidite / dichloromethane / 2 h / 20 °C / Inert atmosphere

With pyridine; bis-triphenylphosphine-palladium(II) chloride; sodium tetrahydroborate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; N-Bromosuccinimide; N-iodo-succinimide; copper(l) iodide; (S)-O,O'-(3,3'-bis(naphthalen-1-ylmethyl)-5,5',6,6'-tetramethyl-1,1'-biphenyl-2,2'-diyl)-N,N-dimethylphosphoramidite; hydrogen; nickel diacetate; ethylenediamine; diethylamine; trifluoroacetic acid; In tetrachloromethane; ethanol; dichloromethane; acetonitrile; 3: Sonogashira coupling;

DOI:10.1016/j.tet.2011.05.125

upstream raw materials:

N-[2-(2,3,4-trimethoxyphenyl)ethyl]-2,2,2-trifluoroacetamide

N-[2-(5-bromo-2,3,4-trimethoxyphenyl)ethyl]-2,2,2-trifluoroacetamide

N-[2-(5-bromo-6-iodo-2,3,4-trimethoxyphenyl)ethyl]-2,2,2-trifluoroacetamide

3-{2-bromo-3,4,5-trimethoxy-6-[2-(trifluoroacetylamino)-ethyl]phenyl}prop-2-ynol