methyl (1S,3S)-1-(3,4-dimethoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3- carboxylate

Base Information

• Chemical Name: methyl (1S,3S)-1-(3,4-dimethoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3- carboxylate
• CAS No.: 380895-64-7
• Molecular Formula: C₂₁H₂₂N₂O₄
• Molecular Weight: 366.417
• Mol file: 380895-64-7.mol

Synonyms:methyl (1S,3S)-1-(3,4-dimethoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3- carboxylate

Chemical Property of methyl (1S,3S)-1-(3,4-dimethoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3- carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (1S,3S)-1-(3,4-dimethoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3- carboxylate

There total 3 articles about methyl (1S,3S)-1-(3,4-dimethoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-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: 28.0%

3,4-dimethoxy-benzaldehyde (120-14-9) + L-tryptophan methyl ester (4299-70-1) → methyl (1R,3S)-1-(3,4-dimethoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3- carboxylate (782478-88-0) + methyl (1S,3S)-1-(3,4-dimethoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3- carboxylate (380895-64-7)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃; for 96h; Inert atmosphere;

DOI:10.2174/157340610793563992

Reference yield:

L-Tryptophan (73-22-3,27732-43-0,80206-30-0,27813-82-7) → methyl (1S,3S)-1-(3,4-dimethoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3- carboxylate (380895-64-7)

Guidance literature:

Multi-step reaction with 2 steps

1: acetyl chloride

2: trifluoroacetic acid / dichloromethane / 96 h / 0 - 20 °C / Inert atmosphere

With acetyl chloride; trifluoroacetic acid; In dichloromethane; 2: Pictet-Spengler cyclisation;

DOI:10.2174/157340610793563992

Reference yield:

L-Tryptophan (73-22-3,27732-43-0,80206-30-0,27813-82-7) → methyl (1R,3S)-1-(3,4-dimethoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3- carboxylate (782478-88-0) + methyl (1S,3S)-1-(3,4-dimethoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3- carboxylate (380895-64-7)

Guidance literature:

Multi-step reaction with 2 steps

1: thionyl chloride / 4 h / 0 - 20 °C

2: toluene-4-sulfonic acid / toluene / 12 h / Reflux

With thionyl chloride; toluene-4-sulfonic acid; In toluene; 2: |Pictet-Spengler Synthesis;

DOI:10.1016/j.bioorg.2015.02.007

upstream raw materials:

3,4-dimethoxy-benzaldehyde

L-tryptophan methyl ester

L-Tryptophan

Downstream raw materials:

(6S,12aS)-2-ethyl-6-(3,4-dimethoxyphenyl)-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione

(6S,12aS)-2-tert-butyl-6-(3,4-dimethoxyphenyl)-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione

(5S,11aS)-4-chlorophenyl-5-(3,4-dimethoxyphenyl)-5,6,11,11a-tetrahydro-1H-imidazo[1',5':1,6]pyrido[3,4-b]indole-1,3(2H)-dione

methyl (1S,3S)-1-(3,4-dimethoxyphenyl)-2-(chloroacetyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylate