(3-(phenyl)-6-methyl-6,11-dihydro-5H-indolizino [6,7-b]indole-1,2-diyl)dimethanol

Base Information

• Chemical Name: (3-(phenyl)-6-methyl-6,11-dihydro-5H-indolizino [6,7-b]indole-1,2-diyl)dimethanol
• CAS No.: 1422377-05-6
• Molecular Formula: C₂₃H₂₂N₂O₂
• Molecular Weight: 358.44
• Mol file: 1422377-05-6.mol

Synonyms:(3-(phenyl)-6-methyl-6,11-dihydro-5H-indolizino [6,7-b]indole-1,2-diyl)dimethanol

Chemical Property of (3-(phenyl)-6-methyl-6,11-dihydro-5H-indolizino [6,7-b]indole-1,2-diyl)dimethanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3-(phenyl)-6-methyl-6,11-dihydro-5H-indolizino [6,7-b]indole-1,2-diyl)dimethanol

There total 5 articles about (3-(phenyl)-6-methyl-6,11-dihydro-5H-indolizino [6,7-b]indole-1,2-diyl)dimethanol 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: 82.0%

dimethyl 3-phenyl-6-methyl-6,11-dihydro-5H-indolizino-[6,7-b]indole-1,2-dicarboxylate (1422376-96-2) → (3-(phenyl)-6-methyl-6,11-dihydro-5H-indolizino [6,7-b]indole-1,2-diyl)dimethanol (1422377-05-6)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; dichloromethane; at -5 - 0 ℃; for 0.5h;

DOI:10.1021/jm301788a

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) → (3-(phenyl)-6-methyl-6,11-dihydro-5H-indolizino [6,7-b]indole-1,2-diyl)dimethanol (1422377-05-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: water; methanol / 5 h / 20 °C

2.1: triethylamine / tetrahydrofuran / 9 h / Reflux

3.1: sodium hydride / mineral oil; tetrahydrofuran / 0.25 h / 0 - 5 °C

3.2: 9 h / 0 - 20 °C

3.3: pH 6

4.1: acetic anhydride / 60 - 75 °C

5.1: lithium aluminium tetrahydride / diethyl ether; dichloromethane / 0.5 h / -5 - 0 °C

With lithium aluminium tetrahydride; acetic anhydride; sodium hydride; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; mineral oil; 1.1: |Pictet-Spengler Synthesis;

DOI:10.1021/jm301788a

Reference yield:

methyl (3S)-1,2,3,4-tetrahydro-β-carboline-3-carboxylate (79815-18-2) → (3-(phenyl)-6-methyl-6,11-dihydro-5H-indolizino [6,7-b]indole-1,2-diyl)dimethanol (1422377-05-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: triethylamine / tetrahydrofuran / 9 h / Reflux

2.1: sodium hydride / mineral oil; tetrahydrofuran / 0.25 h / 0 - 5 °C

2.2: 9 h / 0 - 20 °C

2.3: pH 6

3.1: acetic anhydride / 60 - 75 °C

4.1: lithium aluminium tetrahydride / diethyl ether; dichloromethane / 0.5 h / -5 - 0 °C

With lithium aluminium tetrahydride; acetic anhydride; sodium hydride; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; mineral oil;

DOI:10.1021/jm301788a

upstream raw materials:

(S)-tryptophan methyl ester hydrochloride

methyl (3S)-1,2,3,4-tetrahydro-β-carboline-3-carboxylate

methyl 2-benzoyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate

2-benzoyl-9-methyl-1,2,3,4-tetrahydropyrido[3,4-b]indole-3-carboxylic acid

Downstream raw materials:

[6-methyl-3-phenyl-6,11-dihydro-5H-indolizino [6,7-b]indole-1,2-diyl]bis(methylene)bis(iso propylcarbamate)

[6-methyl-3-phenyl-6,11-dihydro-5H-indolizino [6,7-b]indole-1,2-diyl]bis(methylene)bis(ethylcarbamate)