Ammonium Chloride → HCID 59331940, Verbindung
Reaktionsgleichung
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Mg]Br)=[CH:4][C:3]=1[F:10].[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][C:21](=[O:24])[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].[Cl-].[NH4+]>>[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][C:21]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([F:10])[CH:4]=2)([OH:24])[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:12])[CH3:13]Komponenten
Versuchsvorschrift
A solution of 4-chloro-3-fluorophenylmagnesium bromide (15 ml, 7.5 mmol, 0.5M in THF) was added, under nitrogen, to 4-oxo-piperidine-1-carboxylic acid tert-butyl ester (1.02 g, 5.1 mmol). After 24 hours, saturated ammonium chloride solution was added then the organic solvent was removed in vacuo. The mixture was extracted with ethyl acetate, then this extract was washed with brine, dried (MgSO4), filtered and concentrated to afford a residue which was purified by column chromatography (SiO2), eluting with gradient of ethyl acetate/petrol (0% to 20%) to afford the title compound (511 mg, 30%). 1H NMR (Me-d3-OD) δ 1.48 (9H, s), 1.67 (2H, br.d), 1.92 (2H, td), 3.16-3.29 (2H, m), 3.99 (2H, br.d), 7.27 (1H, dd), 7.38 (1H, dd), 7.42 (1H, t).
Aufarbeitung
- customthe organic solvent was removed in vacuo
- extractionThe mixture was extracted with ethyl acetate
- washthis extract was washed with brine
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated
- customto afford a residue which
- customwas purified by column chromatography (SiO2)
- washeluting with gradient of ethyl acetate/petrol (0% to 20%)
Quellen und Nachweise
- ORD-Eintrag
- ord-baced169e9434bc5b67cf09376bbbfa7
- Quelldatensatz
- uspto-grants-2012_08
- Patentnummer
- US08247576B2
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