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

Base Information

• Chemical Name: (1R,3S)-methyl 1-(3,4-diacetoxyphenyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate
• CAS No.: 1353844-71-9
• Molecular Formula: C₂₃H₂₂N₂O₆
• Molecular Weight: 422.437
• Mol file: 1353844-71-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about (1R,3S)-methyl 1-(3,4-diacetoxyphenyl)-1,2,3,4-tetrahydro-9H-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: 93.0%

3,4-diacetoxybenzaldehyde (67727-64-4) + (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) → (1R,3S)-methyl 1-(3,4-diacetoxyphenyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate (1353844-71-9)

Guidance literature:

3,4-diacetoxybenzaldehyde; (S)-tryptophan methyl ester hydrochloride; In isopropyl alcohol; for 2h; Reflux;

In nitromethane; for 10h; optical yield given as %de; diastereoselective reaction; Reflux;

DOI:10.1016/j.tetasy.2011.10.011

Reference yield:

bis(trichloromethyl) carbonate (32315-10-9) + (1R,3S)-methyl 1-(3,4-diacetoxyphenyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate (1353844-71-9) + isopropylamine (75-31-0) → C26H25N3O6

Guidance literature:

bis(trichloromethyl) carbonate; (1R,3S)-methyl 1-(3,4-diacetoxyphenyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate; With triethylamine; In dichloromethane; at 0 ℃; for 0.266667h;

isopropylamine; In dichloromethane; at 0 ℃; for 3.25h; Reflux;

DOI:10.1016/j.tetasy.2011.10.011

Reference yield:

(1R,3S)-methyl 1-(3,4-diacetoxyphenyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate (1353844-71-9) → (5R,11aS)-2-isopropyl-5-(3,4-dihydroxyphenyl)-6H-1,2,3,5,11,11a-hexahydro-imidazo[1,5-b]-β-carboline-1,3-dione (1353761-83-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine / dichloromethane / 0.27 h / 0 °C

1.2: 3.25 h / 0 °C / Reflux

2.1: methanol; triethylamine / 3 h / Reflux

With methanol; triethylamine; In dichloromethane;

DOI:10.1016/j.tetasy.2011.10.011

upstream raw materials:

3,4-diacetoxybenzaldehyde

(S)-tryptophan methyl ester hydrochloride

Downstream raw materials:

(5R,11aS)-2-isopropyl-5-(3,4-dihydroxyphenyl)-6H-1,2,3,5,11,11a-hexahydro-imidazo[1,5-b]-β-carboline-1,3-dione