Technology Process of (3R,3aS,9R,9aS)-3-((S)-2-nitro-1-phenylethyl)-9-(p-tolyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]quinoline
There total 5 articles about (3R,3aS,9R,9aS)-3-((S)-2-nitro-1-phenylethyl)-9-(p-tolyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]quinoline which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
nitrostyrene; (E)-6-(p-tolyl)hex-5-enal;
With
(2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; acetic acid;
In
dichloromethane;
at -30 ℃;
for 16h;
aniline;
With
toluene-4-sulfonic acid;
In
dichloromethane;
at 4 ℃;
for 24h;
optical yield given as %ee;
enantioselective reaction;
DOI:10.1021/ol201328s
- Guidance literature:
-
Multi-step reaction with 4 steps
1.1: diisobutylaluminium hydride / toluene / -78 °C / Inert atmosphere
1.2: 0 °C
2.1: methylmagnesium bromide / tetrahydrofuran; diethyl ether / -20 °C / Inert atmosphere
2.2: Reflux
2.3: -10 - 20 °C / Inert atmosphere
3.1: pyridinium chlorochromate / dichloromethane / 2 h / 20 °C
4.1: (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; acetic acid / dichloromethane / 16 h / -30 °C
4.2: 24 h / 4 °C
With
(2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; methylmagnesium bromide; diisobutylaluminium hydride; acetic acid; pyridinium chlorochromate;
In
tetrahydrofuran; diethyl ether; dichloromethane; toluene;
4.1: Michael condensation / 4.2: Michael condensation;
DOI:10.1021/ol201328s
- Guidance literature:
-
Multi-step reaction with 2 steps
1.1: pyridinium chlorochromate / dichloromethane / 2 h / 20 °C
2.1: (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; acetic acid / dichloromethane / 16 h / -30 °C
2.2: 24 h / 4 °C
With
(2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; acetic acid; pyridinium chlorochromate;
In
dichloromethane;
2.1: Michael condensation / 2.2: Michael condensation;
DOI:10.1021/ol201328s
