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

Base Information

Chemical Name:(11bS)-8-bromo-11b-phenyl-1,2,5,6,11,11b-hexahydro-3H-indolizino[8,7-b]indol-3-one
CAS No.:1178541-57-5
Molecular Formula:C₂₀H₁₇BrN₂O
Molecular Weight:381.272
Hs Code.:

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

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

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

There total 4 articles about (11bS)-8-bromo-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: 65.0%

: 3610-42-2
5-bromotryptamine

: 5-phenylfuran-2(3H)-one

: 1178541-57-5
(11bS)-8-bromo-11b-phenyl-1,2,5,6,11,11b-hexahydro-3H-indolizino[8,7-b]indol-3-one

Guidance literature:: With (R)-3,3'-bis(triphenylsilyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate; In toluene; at 110 ℃; for 44h; optical yield given as %ee; enantioselective reaction;
DOI:10.1021/ja9024885

Reference yield:

: 85217-69-2,87802-71-9
cinnamyl methyl carbonate

: 1178541-57-5
(11bS)-8-bromo-11b-phenyl-1,2,5,6,11,11b-hexahydro-3H-indolizino[8,7-b]indol-3-one

: 1400791-37-8
(R)-8-bromo-11b-phenyl-5,6,11,11b-tetrahydro-1H-indolizino[8,7-b]indol-3(2H)-one

Guidance literature:: Multi-step reaction with 3 steps

1: C₄₈H₄₉IrNO₂P⁽¹⁺⁾*CF₃O₃S^(1-) / tetrahydrofuran / 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

Reference yield:

: 1400791-55-0
N-(2-(5-bromo-1H-indol-3-yl)ethyl)-N-(1-phenylallyl)acrylamide

: 1178541-57-5
(11bS)-8-bromo-11b-phenyl-1,2,5,6,11,11b-hexahydro-3H-indolizino[8,7-b]indol-3-one

: 1400791-37-8
(R)-8-bromo-11b-phenyl-5,6,11,11b-tetrahydro-1H-indolizino[8,7-b]indol-3(2H)-one

Guidance literature:: With Hoveyda-Grubbs catalyst second generation; (S)-3,3'-bis(triphenylsilyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate; In toluene; Overall yield = 95 %; enantioselective reaction; Inert atmosphere; Reflux; Schlenk technique;
DOI:10.1021/ol302215u DOI:10.1021/ol302215u