{[1-(4-chloro-3-methoxy-phenyl)-1,2,3,4-tetrahydronaphthalen-2-yl]-methyl-amino}-acetic acid methyl ester

Base Information

• Chemical Name: {[1-(4-chloro-3-methoxy-phenyl)-1,2,3,4-tetrahydronaphthalen-2-yl]-methyl-amino}-acetic acid methyl ester
• CAS No.: 1369217-08-2
• Molecular Formula: C₂₁H₂₄ClNO₃
• Molecular Weight: 373.879
• Mol file: 1369217-08-2.mol

Synonyms:

Chemical Property of {[1-(4-chloro-3-methoxy-phenyl)-1,2,3,4-tetrahydronaphthalen-2-yl]-methyl-amino}-acetic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {[1-(4-chloro-3-methoxy-phenyl)-1,2,3,4-tetrahydronaphthalen-2-yl]-methyl-amino}-acetic acid methyl ester

There total 9 articles about {[1-(4-chloro-3-methoxy-phenyl)-1,2,3,4-tetrahydronaphthalen-2-yl]-methyl-amino}-acetic 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:

3-phenyl-propionaldehyde (104-53-0) → {[1-(4-chloro-3-methoxy-phenyl)-1,2,3,4-tetrahydronaphthalen-2-yl]-methyl-amino}-acetic acid methyl ester (1369217-08-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

1.2: 1 h / -78 - 20 °C / Inert atmosphere

2.1: copper(II) bis(trifluoromethanesulfonate); (S,S)-2,2'-isopropylidenebis(4-phenyl-2-oxazoline) / dichloromethane / 3 h / 32 °C / Inert atmosphere; Molecular sieve

2.2: 1 h / 32 °C / Inert atmosphere

3.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

3.2: 4 h / 20 °C / Inert atmosphere

4.1: 4-Methoxybenzenethiol; potassium carbonate / dimethyl sulfoxide; acetonitrile / 5 h / 20 °C / Inert atmosphere

5.1: potassium fluoride on basic alumina / acetonitrile / 24 h / Inert atmosphere; Reflux

With n-butyllithium; 4-Methoxybenzenethiol; potassium fluoride on basic alumina; copper(II) bis(trifluoromethanesulfonate); sodium hydride; (S,S)-2,2'-isopropylidenebis(4-phenyl-2-oxazoline); potassium carbonate; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; acetonitrile; 1.2: Wittig reaction / 2.2: Friedel Crafts alkylation;

DOI:10.1016/j.tetasy.2012.01.017

Reference yield:

4-Phenyl-1-butyne (16520-62-0) → {[1-(4-chloro-3-methoxy-phenyl)-1,2,3,4-tetrahydronaphthalen-2-yl]-methyl-amino}-acetic acid methyl ester (1369217-08-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: benzo[1,3,2]dioxaborole / tetrahydrofuran / 3 h / Reflux; Inert atmosphere

1.2: 0.42 h / 20 °C / Inert atmosphere

1.3: 12 h / Reflux

2.1: copper(II) bis(trifluoromethanesulfonate); (S,S)-2,2'-isopropylidenebis(4-phenyl-2-oxazoline) / dichloromethane / 1 h / 25 °C / Inert atmosphere; Molecular sieve

2.2: 1 h / 25 °C / Inert atmosphere

3.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

3.2: 4 h / 20 °C / Inert atmosphere

4.1: 4-Methoxybenzenethiol; potassium carbonate / dimethyl sulfoxide; acetonitrile / 5 h / 20 °C / Inert atmosphere

5.1: potassium fluoride on basic alumina / acetonitrile / 24 h / Inert atmosphere; Reflux

With 4-Methoxybenzenethiol; potassium fluoride on basic alumina; copper(II) bis(trifluoromethanesulfonate); sodium hydride; (S,S)-2,2'-isopropylidenebis(4-phenyl-2-oxazoline); potassium carbonate; benzo[1,3,2]dioxaborole; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; acetonitrile; 2.2: Friedel Crafts alkylation;

DOI:10.1016/j.tetasy.2012.01.017

Reference yield:

4-chloro-3-methoxyphenylmethyl(triphenyl)phosphonium bromide (110463-12-2) → {[1-(4-chloro-3-methoxy-phenyl)-1,2,3,4-tetrahydronaphthalen-2-yl]-methyl-amino}-acetic acid methyl ester (1369217-08-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

1.2: 1 h / -78 - 20 °C / Inert atmosphere

2.1: copper(II) bis(trifluoromethanesulfonate); (S,S)-2,2'-isopropylidenebis(4-phenyl-2-oxazoline) / dichloromethane / 3 h / 32 °C / Inert atmosphere; Molecular sieve

2.2: 1 h / 32 °C / Inert atmosphere

3.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

3.2: 4 h / 20 °C / Inert atmosphere

4.1: 4-Methoxybenzenethiol; potassium carbonate / dimethyl sulfoxide; acetonitrile / 5 h / 20 °C / Inert atmosphere

5.1: potassium fluoride on basic alumina / acetonitrile / 24 h / Inert atmosphere; Reflux

With n-butyllithium; 4-Methoxybenzenethiol; potassium fluoride on basic alumina; copper(II) bis(trifluoromethanesulfonate); sodium hydride; (S,S)-2,2'-isopropylidenebis(4-phenyl-2-oxazoline); potassium carbonate; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; acetonitrile; 1.2: Wittig reaction / 2.2: Friedel Crafts alkylation;

DOI:10.1016/j.tetasy.2012.01.017

upstream raw materials:

3-phenyl-propionaldehyde

1-bromo-2,2-dimethoxyethane

(+)-trans-N-[1-(4-chloro-3-methoxy-phenyl)-1,2,3,4-tetrahydronaphthalen-2-yl]-methylamine

1-chloro-2-methoxy-4-(4-phenyl-but-1-enyl)-benzene