Sodium Iodide → (2R)-1-[3-(4-iodophenoxy)propyl]-2-methylpyrrolidine

HRID 215759

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]=1

Komponenten

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-8f4c30c8705148e7a0a39fc309356f2a
Quelldatensatz: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08193176B2

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