13b-hydroxy-7,8,13,13b-tetrahydro-5H-benzo[1,2]indolizino[8,7-b]indol-5-one

Base Information

• Chemical Name: 13b-hydroxy-7,8,13,13b-tetrahydro-5H-benzo[1,2]indolizino[8,7-b]indol-5-one
• CAS No.: 76504-07-9
• Molecular Formula: C₁₈H₁₄N₂O₂
• Molecular Weight: 290.321
• Mol file: 76504-07-9.mol

Synonyms:13b-hydroxy-7,8,13,13b-tetrahydro-5H-benzo[1,2]indolizino[8,7-b]indol-5-one

Chemical Property of 13b-hydroxy-7,8,13,13b-tetrahydro-5H-benzo[1,2]indolizino[8,7-b]indol-5-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 13b-hydroxy-7,8,13,13b-tetrahydro-5H-benzo[1,2]indolizino[8,7-b]indol-5-one

There total 2 articles about 13b-hydroxy-7,8,13,13b-tetrahydro-5H-benzo[1,2]indolizino[8,7-b]indol-5-one 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:

phthalic anhydride (85-44-9) → 13b-hydroxy-7,8,13,13b-tetrahydro-5H-benzo[1,2]indolizino[8,7-b]indol-5-one (76504-07-9)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene / Inert atmosphere; Reflux

2: trifluorormethanesulfonic acid / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

With trifluorormethanesulfonic acid; In dichloromethane; toluene;

DOI:10.1021/ol400995c

Reference yield:

N-phthalimidotryptamine (15741-71-6) → 2-hydroxymethyl-N-(2-indol-3-yl-ethyl)-benzamide (59048-78-1) + 13b-hydroxy-7,8,13,13b-tetrahydro-5H-benzo[1,2]indolizino[8,7-b]indol-5-one (76504-07-9) + 3-hydroxy-2-(2-indol-3-yl-ethyl)-2,3-dihydro-isoindol-1-one (65020-18-0)

Guidance literature:

With sodium tetrahydroborate; copper dichloride; In ethanol; at 0 ℃; for 0.166667h; Other catalysts;

DOI:10.1016/S0040-4039(00)77834-8

Reference yield:

5-benzyloxy-1H-indole (1215-59-4) + 13b-hydroxy-7,8,13,13b-tetrahydro-5H-benzo[1,2]indolizino[8,7-b]indol-5-one (76504-07-9) → (R)-13b-(5-benzyloxy-1H-indol-3-yl)-7,8,13,13b-tetrahydro-5H-benzo[1,2]indolizino[8,7-b]indol-5-one + (S)-13b-(5-benzyloxy-1H-indol-3-yl)-7,8,13,13b-tetrahydro-5H-benzo[1,2]indolizino[8,7-b]indol-5-one

Guidance literature:

With (S)-(+)-3,3′-bis(3,5-bis(trifluoromethyl)phenyl)-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate; In 1,4-dioxane; at 20 ℃; for 3h; Overall yield = 99 %; Overall yield = 49 mg; enantioselective reaction;

DOI:10.1039/c5ob00175g

upstream raw materials:

N-phthalimidotryptamine

phthalic anhydride

Refernces

• 1、 Atta-ur-Rahman,Ghazala,Sultana,Bashir. "Metal ion-catalysed reduction of indolic imides, a facile β-carboline synthesis". . p. 1773 - 1774. Retrieved 2007/10/02.