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

Base Information

• Chemical Name: (1S,3S)-methyl 1-(4-hydroxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate
• CAS No.: 1239919-29-9
• Molecular Formula: C₁₉H₁₈N₂O₃
• Molecular Weight: 322.364
• Mol file: 1239919-29-9.mol

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

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

There total 4 articles about (1S,3S)-methyl 1-(4-hydroxyphenyl)-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:

(S)-tryptophan methyl ester hydrochloride (7524-52-9,26988-71-6,5619-09-0,14907-27-8,41222-70-2,67557-19-1,109492-62-8) + 4-hydroxy-benzaldehyde (123-08-0,65581-83-1) → (1S,3S)-methyl 1-(4-hydroxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate (1239919-29-9) + methyl (1R,3S)-1-(4-hydroxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate

Guidance literature:

With trifluoroacetic acid; In water; at 20 ℃; for 12h; Overall yield = 65 percent; Overall yield = 0.41 g;

DOI:10.1016/j.ejmech.2019.111919

Reference yield:

L-Tryptophan (73-22-3,27732-43-0,80206-30-0,27813-82-7) → (1S,3S)-methyl 1-(4-hydroxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate (1239919-29-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: thionyl chloride / 5 °C / Reflux

1.2: 4 h / Reflux

2.1: isopropyl alcohol / 4 h / Reflux

2.2: 10 h / Reflux

3.1: sodium carbonate / water

With thionyl chloride; sodium carbonate; In water; isopropyl alcohol; 2.1: |Pictet-Spengler Synthesis;

DOI:10.1002/chir.22193

Reference yield:

(S)-tryptophan methyl ester hydrochloride (7524-52-9,26988-71-6,5619-09-0,14907-27-8,41222-70-2,67557-19-1,109492-62-8) → (1S,3S)-methyl 1-(4-hydroxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate (1239919-29-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: isopropyl alcohol / 4 h / Reflux

1.2: 10 h / Reflux

2.1: sodium carbonate / water

With sodium carbonate; In water; isopropyl alcohol; 1.1: |Pictet-Spengler Synthesis;

DOI:10.1002/chir.22193

upstream raw materials:

L-Tryptophan

(S)-tryptophan methyl ester hydrochloride

4-hydroxy-benzaldehyde