Technology Process of (3R,4aS,9S,9aR)-7-bromo-9-(4-bromophenyl)-3-propyl-1,2,3,4,4a,9,9a,10-octahydroacridine-2,2(9H)-dicarbonitrile
There total 4 articles about (3R,4aS,9S,9aR)-7-bromo-9-(4-bromophenyl)-3-propyl-1,2,3,4,4a,9,9a,10-octahydroacridine-2,2(9H)-dicarbonitrile which
guide to synthetic route it.
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synthetic route:
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(3S,4aR,9R,9aS)-7-bromo-9-(4-bromophenyl)-3-propyl-1,2,3,4,4a,9,9a,10-octahydroacridine-2,2(9H)-dicarbonitrile
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1277185-04-2
(3R,4aS,9S,9aR)-7-bromo-9-(4-bromophenyl)-3-propyl-1,2,3,4,4a,9,9a,10-octahydroacridine-2,2(9H)-dicarbonitrile
- Guidance literature:
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(E)-2-Hexenal; (E)-2-(3-(4-bromophenyl)allyl)malononitrile;
With
(S)-2-{bis[3,5-bis(trifluoromethyl)phenyl][(trimethylsilanyl)oxy]methyl}pyrrolidine; benzoic acid;
In
dichloromethane;
at 20 ℃;
for 24h;
4-bromo-aniline;
With
trifluoroacetic acid;
In
dichloromethane;
at -30 ℃;
for 48h;
optical yield given as %ee;
enantioselective reaction;
DOI:10.1002/anie.201006608
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(3S,4aR,9R,9aS)-7-bromo-9-(4-bromophenyl)-3-propyl-1,2,3,4,4a,9,9a,10-octahydroacridine-2,2(9H)-dicarbonitrile
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1277185-04-2
(3R,4aS,9S,9aR)-7-bromo-9-(4-bromophenyl)-3-propyl-1,2,3,4,4a,9,9a,10-octahydroacridine-2,2(9H)-dicarbonitrile
- Guidance literature:
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Multi-step reaction with 4 steps
1.1: diisobutylaluminium hydride / toluene / 3 h / -78 °C / Inert atmosphere
2.1: phosphorus tribromide / tetrachloromethane / 2 h / 0 °C
3.1: potassium carbonate / tetrahydrofuran / 0 - 20 °C
4.1: (S)-2-{bis[3,5-bis(trifluoromethyl)phenyl][(trimethylsilanyl)oxy]methyl}pyrrolidine; benzoic acid / dichloromethane / 24 h / 20 °C
4.2: 48 h / -30 °C
With
(S)-2-{bis[3,5-bis(trifluoromethyl)phenyl][(trimethylsilanyl)oxy]methyl}pyrrolidine; phosphorus tribromide; diisobutylaluminium hydride; potassium carbonate; benzoic acid;
In
tetrahydrofuran; tetrachloromethane; dichloromethane; toluene;
4.1: Michael addition;
DOI:10.1002/anie.201006608
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(3S,4aR,9R,9aS)-7-bromo-9-(4-bromophenyl)-3-propyl-1,2,3,4,4a,9,9a,10-octahydroacridine-2,2(9H)-dicarbonitrile
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1277185-04-2
(3R,4aS,9S,9aR)-7-bromo-9-(4-bromophenyl)-3-propyl-1,2,3,4,4a,9,9a,10-octahydroacridine-2,2(9H)-dicarbonitrile
- Guidance literature:
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Multi-step reaction with 5 steps
1.1: thionyl chloride / 2 h / 0 °C / Reflux
2.1: diisobutylaluminium hydride / toluene / 3 h / -78 °C / Inert atmosphere
3.1: phosphorus tribromide / tetrachloromethane / 2 h / 0 °C
4.1: potassium carbonate / tetrahydrofuran / 0 - 20 °C
5.1: (S)-2-{bis[3,5-bis(trifluoromethyl)phenyl][(trimethylsilanyl)oxy]methyl}pyrrolidine; benzoic acid / dichloromethane / 24 h / 20 °C
5.2: 48 h / -30 °C
With
(S)-2-{bis[3,5-bis(trifluoromethyl)phenyl][(trimethylsilanyl)oxy]methyl}pyrrolidine; thionyl chloride; phosphorus tribromide; diisobutylaluminium hydride; potassium carbonate; benzoic acid;
In
tetrahydrofuran; tetrachloromethane; dichloromethane; toluene;
5.1: Michael addition;
DOI:10.1002/anie.201006608
