Technology Process of (-)-N-((2S,3S)-3-hydroxy-1-cyclohexyl-4-pentenyl)benzamide
There total 14 articles about (-)-N-((2S,3S)-3-hydroxy-1-cyclohexyl-4-pentenyl)benzamide which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
hydrogenchloride;
In
tetrahydrofuran; methanol;
DOI:10.1021/jo991065r
- Guidance literature:
-
Multi-step reaction with 4 steps
1: lithium aluminum hydride / tetrahydrofuran / 6 h / Heating
2: sodium hydroxide / tetrahydrofuran; H2O / 0.5 h / 20 °C
3: oxalyl chloride; dimethyl sulfoxide; diisopropylethylamine / CH2Cl2 / -60 - -35 °C
4: CH2Cl2; tetrahydrofuran / 1 h / 0 °C
With
sodium hydroxide; lithium aluminium tetrahydride; oxalyl dichloride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; dichloromethane; water;
1: Reduction / 2: Acylation / 3: Oxidation / 4: Addition;
DOI:10.1021/jo991065r
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: benzene / 0.5 h / 30 °C
2.1: BF3*Et2O / CH2Cl2 / 0.25 h / -78 °C
2.2: 86 percent / diisobutylaluminum hydride / CH2Cl2; hexane / 2 h / -78 °C
3.1: HCl / H2O; ethyl acetate / 0.5 h
4.1: H2O; ethyl acetate / 2 h
5.1: pyridine / CH2Cl2 / 12 h
6.1: tetrakis(triphenylphosphine)palladium(0); potassium carbonate / acetonitrile / 24 h / Heating
7.1: HCl / methanol; tetrahydrofuran
With
pyridine; hydrogenchloride; tetrakis(triphenylphosphine) palladium(0); boron trifluoride diethyl etherate; potassium carbonate;
In
tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; acetonitrile; benzene;
1.1: olefination; Wittig reaction / 2.1: Reduction / 2.2: Reduction / 3.1: Hydrolysis / 4.1: Acylation / 5.1: Acetylation / 6.1: Cyclization / 7.1: Hydrolysis;
DOI:10.1021/jo991065r