Reaktionsgleichung
[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][NH:3]1.[C:8]([C:10]1[CH:11]=[C:12]([CH:17]=[CH:18][C:19]=1F)[C:13]([O:15]C)=[O:14])#[N:9].[Li+].[OH-]>CN(C=O)C.O>[C:8]([C:10]1[CH:11]=[C:12]([CH:17]=[CH:18][C:19]=1[N:3]1[CH2:4][CH2:5][CH2:6][CH2:7][CH:2]1[CH3:1])[C:13]([OH:15])=[O:14])#[N:9]Komponenten
Versuchsvorschrift
2-Methylpiperidine (744 mg; 7.5 mmol; 5 eq.) was added to a solution of methyl 3-cyano-4-fluorobenzoate (269 mg; 1.5 mmol; 1 eq.) in DMF (2 mL) and the resulting mixture was stirred at room temperature for 2 days. The solution was partitioned between ethyl acetate and water and the phases separated. The organic layer was washed with HCl 0.1M then brine, dried over magnesium sulfate and concentrated in vacuo. The residue was taken up in THF (5 mL) and LiOH (126 mg; 3 mmol; 2 eq.) then water (5 mL) were added and the reaction mixture was stirred at room temperature for 5 hours. The resulting solution was diluted with water and washed with Et2O. The aqueous layer was acidified to pH 2 with HCl 0.1M and extracted with ethyl acetate. The organic phase was dried over magnesium sulfate and concentrated in vacuo to afford the title compound (294 mg, 80%) as an off-white solid.
Aufarbeitung
- customThe solution was partitioned between ethyl acetate and water
- customthe phases separated
- washThe organic layer was washed with HCl 0.1M
- dry with materialbrine, dried over magnesium sulfate
- concentrationconcentrated in vacuo
- stirringthe reaction mixture was stirred at room temperature for 5 hours
- washwashed with Et2O
- extractionextracted with ethyl acetate
- dry with materialThe organic phase was dried over magnesium sulfate
- concentrationconcentrated in vacuo
Quellen und Nachweise
- ORD-Eintrag
- ord-6bc00f824d174c799cec5f645b14d410
- Quelldatensatz
- uspto-grants-2014_11
- Patentnummer
- US08889668B2
Verknüpfte Notizen
Wird geladen…