(11bS)-11b-phenyl-1,2,5,6,11,11b-hexahydro-3H-indolizino[8,7-b]indol-3-one

Base Information

• Chemical Name: (11bS)-11b-phenyl-1,2,5,6,11,11b-hexahydro-3H-indolizino[8,7-b]indol-3-one
• CAS No.: 959979-05-6
• Molecular Formula: C₂₀H₁₈N₂O
• Molecular Weight: 302.376
• Mol file: 959979-05-6.mol

Synonyms:(11bS)-11b-phenyl-1,2,5,6,11,11b-hexahydro-3H-indolizino[8,7-b]indol-3-one

Chemical Property of (11bS)-11b-phenyl-1,2,5,6,11,11b-hexahydro-3H-indolizino[8,7-b]indol-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (11bS)-11b-phenyl-1,2,5,6,11,11b-hexahydro-3H-indolizino[8,7-b]indol-3-one

There total 6 articles about (11bS)-11b-phenyl-1,2,5,6,11,11b-hexahydro-3H-indolizino[8,7-b]indol-3-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:

5-hydroxy-1-[2-(1H-indol-3-yl)ethyl]-5-phenylpyrrolidin-2-one (959979-04-5) → (11bS)-11b-phenyl-1,2,5,6,11,11b-hexahydro-3H-indolizino[8,7-b]indol-3-one (959979-05-6) + (11bR)-11b-phenyl-1,2,5,6,11,11b-hexahydro-3H-indolizino[8,7-b]indol-3-one

Guidance literature:

With chloro-trimethyl-silane; R,R-derivative of cyclohexyl-carbamothioyl-L-valinamide; In various solvent(s); at -78 ℃; for 48h; Title compound not separated from byproducts.;

DOI:10.1021/ja076179w

Reference yield:

N-(2-(1H-indol-3-yl)ethyl)-1-phenylprop-2-en-1-amine (1400791-67-4) → (11bS)-11b-phenyl-1,2,5,6,11,11b-hexahydro-3H-indolizino[8,7-b]indol-3-one (959979-05-6) + (11bR)-11b-phenyl-1,2,5,6,11,11b-hexahydro-3H-indolizino[8,7-b]indol-3-one

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / dichloromethane / 20 °C / Inert atmosphere

2: Hoveyda-Grubbs catalyst second generation; (S)-3,3'-bis(triphenylsilyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate / toluene / Inert atmosphere; Reflux; Schlenk technique

With Hoveyda-Grubbs catalyst second generation; (S)-3,3'-bis(triphenylsilyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate; triethylamine; In dichloromethane; toluene;

DOI:10.1021/ol302215u DOI:10.1021/ol302215u

Reference yield:

tryptamine (61-54-1) → (11bS)-11b-phenyl-1,2,5,6,11,11b-hexahydro-3H-indolizino[8,7-b]indol-3-one (959979-05-6) + (11bR)-11b-phenyl-1,2,5,6,11,11b-hexahydro-3H-indolizino[8,7-b]indol-3-one

Guidance literature:

Multi-step reaction with 3 steps

1: C₄₈H₄₉IrNO₂P⁽¹⁺⁾*CF₃O₃S^(1-) / tetrahydrofuran / 0.5 h / 50 °C / Schlenk technique; Inert atmosphere

2: triethylamine / dichloromethane / 20 °C / Inert atmosphere

3: Hoveyda-Grubbs catalyst second generation; (S)-3,3'-bis(triphenylsilyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate / toluene / Inert atmosphere; Reflux; Schlenk technique

With Hoveyda-Grubbs catalyst second generation; (S)-3,3'-bis(triphenylsilyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate; C₄₈H₄₉IrNO₂P⁽¹⁺⁾*CF₃O₃S^(1-); triethylamine; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1021/ol302215u DOI:10.1021/ol302215u

upstream raw materials:

5-hydroxy-1-[2-(1H-indol-3-yl)ethyl]-5-phenylpyrrolidin-2-one

N-(2-(1H-indol-3-yl)ethyl)-N-(1-phenylallyl)acrylamide

N-(2-(1H-indol-3-yl)ethyl)-1-phenylprop-2-en-1-amine

tryptamine