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

Base Information

• Chemical Name: (1S,3S)-methyl 1-(4-hydroxy-3-methoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate hydrochloride
• CAS No.: 1352308-77-0
• Molecular Formula: C₂₀H₂₀N₂O₄*ClH
• Molecular Weight: 388.851

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

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

Chemical Property:

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

There total 4 articles about (1S,3S)-methyl 1-(4-hydroxy-3-methoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate hydrochloride 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: 96.0%

C20H20N2O4*ClH → (1S,3S)-methyl 1-(4-hydroxy-3-methoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate hydrochloride (1352308-77-0)

Guidance literature:

With sodium chloride; In water; at 95 ℃; for 4h; diastereoselective reaction; Green chemistry;

DOI:10.1039/c7ra08811f

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) + vanillin (121-33-5,8014-42-4) → (1S,3S)-methyl 1-(4-hydroxy-3-methoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate hydrochloride (1352308-77-0)

Guidance literature:

Multi-step reaction with 2 steps

1: isopropyl alcohol / Reflux; Green chemistry

2: sodium chloride / water / 4 h / 95 °C / Green chemistry

With sodium chloride; In water; isopropyl alcohol; 1: |Pictet-Spengler Synthesis;

DOI:10.1039/c7ra08811f

Reference yield:

L-Tryptophan (73-22-3,27732-43-0,80206-30-0,27813-82-7) → (1S,3S)-methyl 1-(4-hydroxy-3-methoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate hydrochloride (1352308-77-0)

Guidance literature:

Multi-step reaction with 2 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

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

DOI:10.1002/chir.22193

upstream raw materials:

L-Tryptophan

(S)-tryptophan methyl ester hydrochloride

vanillin

Downstream raw materials:

(5aS,12S,14aS)-12-(4-hydroxy-3-methoxyphenyl)-1,2,3,5a,6,14ahexahydropyrrolo[1'',2'':4',5']pyrazino[1',2':1,6]pyrido[3,4-b]indole-5,14(11H,12H)-dione

C₄₀H₃₇N₃O₇

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