Sodium Iodide → (2R)-1-[3-(4-iodophenoxy)propyl]-2-methylpyrrolidine
Reaktionsgleichung
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([I:12])=[CH:8][CH:7]=1.[CH3:13][C@@H:14]1[CH2:18][CH2:17][CH2:16][NH:15]1.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O>[I:12][C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH2:3][CH2:2][N:15]2[CH2:16][CH2:17][CH2:18][C@H:14]2[CH3:13])=[CH:7][CH:8]=1Komponenten
7
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 100 °C
Versuchsvorschrift
A suspension of 1-(3-chloropropoxy)-4-iodobenzene obtained in Example 1-(1) (2.79 g), (R)-2-methylpyrrolidine (0.961 g), sodium iodide (0.282 g) and potassium carbonate (2.60 g) in acetonitrile (2.8 mL) was stirred in a sealed tube at 100° C. for 5 hours. The reaction mixture was cooled to room temperature, diluted with water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluting solvent: n-hexane:ethyl acetate=10:1) to give the titled compound (3.27 g) as a yellow oil.
Aufarbeitung
- temperatureThe reaction mixture was cooled to room temperature
- extractionextracted with ethyl acetate
- washThe organic layer was washed with water and brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated under reduced pressure
- customThe resulting residue was purified by silica gel column chromatography (eluting solvent: n-hexane:ethyl acetate=10:1)
Quellen und Nachweise
- ORD-Eintrag
- ord-8fe2dd441f9b4730ad763dcbf7990218
- Quelldatensatz
- uspto-grants-2012_05
- Patentnummer
- US08183387B2
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