11-(4-methoxy-benzyl)-1-oxo-2,3,6,11-tetrahydro-1H,5H-indolizino[8,7-b]indole-11b-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: 11-(4-methoxy-benzyl)-1-oxo-2,3,6,11-tetrahydro-1H,5H-indolizino[8,7-b]indole-11b-carboxylic acid tert-butyl ester
• CAS No.: 918803-44-8
• Molecular Formula: C₂₇H₃₀N₂O₄
• Molecular Weight: 446.546
• Mol file: 918803-44-8.mol

Synonyms:11-(4-methoxy-benzyl)-1-oxo-2,3,6,11-tetrahydro-1H,5H-indolizino[8,7-b]indole-11b-carboxylic acid tert-butyl ester

Chemical Property of 11-(4-methoxy-benzyl)-1-oxo-2,3,6,11-tetrahydro-1H,5H-indolizino[8,7-b]indole-11b-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 11-(4-methoxy-benzyl)-1-oxo-2,3,6,11-tetrahydro-1H,5H-indolizino[8,7-b]indole-11b-carboxylic acid tert-butyl ester

There total 1 articles about 11-(4-methoxy-benzyl)-1-oxo-2,3,6,11-tetrahydro-1H,5H-indolizino[8,7-b]indole-11b-carboxylic acid tert-butyl ester 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: 75.0%

5-Chloro-2,3-dioxo-pentanoic acid tert-butyl ester (117917-42-7) + 2-(1-(4-methoxybenzyl)-1H-indol-3-yl)ethan-1-amine (157561-19-8) → 11-(4-methoxy-benzyl)-1-oxo-2,3,6,11-tetrahydro-1H,5H-indolizino[8,7-b]indole-11b-carboxylic acid tert-butyl ester (918803-44-8)

Guidance literature:

In acetonitrile; at 20 ℃; for 8h;

DOI:10.1021/jo061724h

Reference yield: 86.0%

11-(4-methoxy-benzyl)-1-oxo-2,3,6,11-tetrahydro-1H,5H-indolizino[8,7-b]indole-11b-carboxylic acid tert-butyl ester (918803-44-8) → 12-(4-methoxy-benzyl)-10-oxo-5,6,7,8,9,10,11,12-octahydro-7,12-diaza-cyclonona[a]indene-11-carboxylic acid tert-butyl ester (918803-45-9)

Guidance literature:

With samarium diiodide; In tetrahydrofuran; at 20 ℃; for 3h;

DOI:10.1021/jo061724h

Reference yield:

11-(4-methoxy-benzyl)-1-oxo-2,3,6,11-tetrahydro-1H,5H-indolizino[8,7-b]indole-11b-carboxylic acid tert-butyl ester (918803-44-8) → C25H26N2O2 (918803-48-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 86 percent / SmI₂ / tetrahydrofuran / 3 h / 20 °C

2.1: 83 percent / hydrochloric acid / ethanol; H₂O / 1 h / 20 °C

3.1: LDA / hexane; tetrahydrofuran / 1 h / -78 °C

3.2: diethyl ether; tetrahydrofuran; hexane / 1 h / -78 °C

4.1: 747 mg / DMAP; DBU; trifluoroacetic anhydride / CH₂Cl₂ / -42 - 20 °C

5.1: 53 percent / anhydrous AlCl₃ / benzene / 4 h / 20 °C

With hydrogenchloride; dmap; aluminium trichloride; samarium diiodide; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic anhydride; lithium diisopropyl amide; In tetrahydrofuran; ethanol; hexane; dichloromethane; water; benzene; 2.1: Mannich reaction / 3.2: aldol condensation;

DOI:10.1021/jo061724h

upstream raw materials:

5-Chloro-2,3-dioxo-pentanoic acid tert-butyl ester

2-(1-(4-methoxybenzyl)-1H-indol-3-yl)ethan-1-amine

Downstream raw materials:

12-(4-methoxy-benzyl)-10-oxo-5,6,7,8,9,10,11,12-octahydro-7,12-diaza-cyclonona[a]indene-11-carboxylic acid tert-butyl ester

C₂₅H₂₆N₂O₂

C₂₈H₃₂N₂O₄