Reaktionsgleichung
Cl[CH2:2][CH2:3][CH2:4][CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.[NH2:11][CH2:12][CH:13]=[O:14].[I-].[Na+].[C:17](=[O:20])([O-])[O-].[K+].[K+].[CH3:23]N(C)C=O>O>[CH:5]1([CH2:4][CH2:3][CH2:2][NH:11][CH2:12][CH:13]([O:20][CH3:17])[O:14][CH3:23])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1Komponenten
Versuchsvorschrift
1-Chloro-3-cyclohexylpropane (11.1 g, 69.0 mmol), 2-aminoacetaldehyde (15.0 mL, 138.0 mmol, 2.0 equiv), and sodium iodide (2.1 g, 14.0 mmol, 0.2 equiv) were combined in anhydrous N,N-dimethylformamide (20 mL). The solution was stirred over solid potassium carbonate (9.66 g, 70 mmol) at 80° C. for 16 hours. The mixture was cooled to room temperature and diluted with water. The solution was extracted with ethyl acetate (2×). The combined organic phase was washed with brine (3×), dried (MgSO4), and concentrated in vacuo to a crude oil. Silica gel chromatography (gradient elution from 50:50 hexane/ethyl acetate to 100% ethyl acetate) yielded the title compound as a yellow oil (12.0 g, 76%). 1H NMR (CDCl3, 300 MHz) δ 4.46 (t, 5.5 Hz, 1 H), 3.38 (s, 6 H), 2.71 (d, 5.5 Hz, 2 H), 2.57 (t, 7.4 Hz, 2 H), 1.75-1.60 (m, 3 H), 1.47 (m, 2 H), 1.17 (m, 8 H), 0.86 (m, 2 H); Rf =0.27 (50:50 hexane/ethyl acetate).
Aufarbeitung
- extractionThe solution was extracted with ethyl acetate (2×)
- washThe combined organic phase was washed with brine (3×)
- dry with materialdried (MgSO4)
- concentrationconcentrated in vacuo to a crude oil
- washSilica gel chromatography (gradient elution from 50:50 hexane/ethyl acetate to 100% ethyl acetate)
Quellen und Nachweise
- ORD-Eintrag
- ord-49a9bf55d13948c788adc27ecbd9a7ce
- Quelldatensatz
- uspto-grants-2000_04
- Patentnummer
- US06051586
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