(13S,11bS)-13-(4-bromophenyl)-2,3,4,5,6,11b,12,13-octahydro-1-oxo-11H-4b,11-diazaindeno[2,1-a]phenanthrene

Base Information

Chemical Name:(13S,11bS)-13-(4-bromophenyl)-2,3,4,5,6,11b,12,13-octahydro-1-oxo-11H-4b,11-diazaindeno[2,1-a]phenanthrene
CAS No.:1334229-55-8
Molecular Formula:C₂₅H₂₃BrN₂O
Molecular Weight:447.374
Hs Code.:

Synonyms:(13S,11bS)-13-(4-bromophenyl)-2,3,4,5,6,11b,12,13-octahydro-1-oxo-11H-4b,11-diazaindeno[2,1-a]phenanthrene

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Chemical Property of (13S,11bS)-13-(4-bromophenyl)-2,3,4,5,6,11b,12,13-octahydro-1-oxo-11H-4b,11-diazaindeno[2,1-a]phenanthrene

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Technology Process of (13S,11bS)-13-(4-bromophenyl)-2,3,4,5,6,11b,12,13-octahydro-1-oxo-11H-4b,11-diazaindeno[2,1-a]phenanthrene

There total 4 articles about (13S,11bS)-13-(4-bromophenyl)-2,3,4,5,6,11b,12,13-octahydro-1-oxo-11H-4b,11-diazaindeno[2,1-a]phenanthrene 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:

: 61-54-1
tryptamine

: 1062118-01-7
(4S)-4-(4-bromophenyl)-2-hydroxy-3,4,7,8-tetrahydro-2H-chromen-5(6H)-one

: 1334229-55-8
(13S,11bS)-13-(4-bromophenyl)-2,3,4,5,6,11b,12,13-octahydro-1-oxo-11H-4b,11-diazaindeno[2,1-a]phenanthrene

: (13S,11bR)-13-(4-bromophenyl)-2,3,4,5,6,11b,12,13-octahydro-1-oxo-11H-4b,11-diazaindeno[2,1-a]phenanthrene

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at 50 ℃; for 12h; optical yield given as %de; diastereoselective reaction;
DOI:10.1016/j.tet.2011.07.050

Reference yield:

: 61-54-1
tryptamine

: 1062118-01-7
(4S)-4-(4-bromophenyl)-2-hydroxy-3,4,7,8-tetrahydro-2H-chromen-5(6H)-one

: 1334229-55-8
(13S,11bS)-13-(4-bromophenyl)-2,3,4,5,6,11b,12,13-octahydro-1-oxo-11H-4b,11-diazaindeno[2,1-a]phenanthrene

Guidance literature:: With acetic acid; In dichloromethane; at 50 ℃; diastereoselective reaction;
DOI:10.1002/adsc.201100258

Reference yield:

: 49678-04-8,3893-18-3
4-bromocinnamaldeyde

: 1334229-55-8
(13S,11bS)-13-(4-bromophenyl)-2,3,4,5,6,11b,12,13-octahydro-1-oxo-11H-4b,11-diazaindeno[2,1-a]phenanthrene

Guidance literature:: Multi-step reaction with 2 steps

1.1: (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine / dichloromethane / 0.17 h / 0 °C

1.2: 0 °C

2.1: acetic acid / dichloromethane / 50 °C

With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; acetic acid; In dichloromethane; 1.1: Michael condensation / 1.2: Michael condensation / 2.1: Pictet-Spengler cyclisation;
DOI:10.1002/adsc.201100258