Ethanol → Ethyl 1-amino-2,3-dihydro-1H-indene-1-carboxylate
Reaktionsgleichung
S(Cl)(Cl)=O.[NH2:5][C:6]1([C:15]([OH:17])=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7]1.[CH2:18](O)[CH3:19]>>[NH2:5][C:6]1([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7]1Komponenten
Versuchsvorschrift
Thionyl chloride (0.617 mL, 8.465 mmol) was added dropwise to anhydrous ethanol (6 mL) cooled to −30° followed by 1-amino-2,3-dihydro-1H-indene-1-carboxylic acid (0.300 g, 1.693 mmol) the reaction was then refluxed for 4 hours. The reaction was concentrated by rotary evaporation and diluted with water (5 mL) and the pH was adjusted to 9 with 6N aqueous sodium hydroxide. The solution was extracted with ethyl acetate (2×25 mL) and the organic extracts were washed with brine (25 mL), dried over sodium sulfate, filtered, and concentrated by rotary evaporation to afford the title compound as an oil (0.293 g, 1.43 mmol, 84%). 1H NMR (300 MHz, DMSO-D6) δ ppm 1.12 (t, J=7.17 Hz, 3 H) 1.85-2.07 (m, 1 H) 2.31 (s, 2 H) 2.51-2.66 (m, 1 H) 2.93 (t, J=6.99 Hz, 2 H) 3.90-4.21 (m, 2 H) 7.13-7.34 (m, 4 H). MS (DCI) m/z 206 (M+H)+, 223 (M+NH4)+.
Aufarbeitung
- temperaturecooled to −30°
- temperaturewas then refluxed for 4 hours
- concentrationThe reaction was concentrated by rotary evaporation
- additiondiluted with water (5 mL)
- extractionThe solution was extracted with ethyl acetate (2×25 mL)
- washthe organic extracts were washed with brine (25 mL)
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated by rotary evaporation
Quellen und Nachweise
- ORD-Eintrag
- ord-734c07ed12e44c7dabfbceee2bce657e
- Quelldatensatz
- uspto-grants-2011_03
- Patentnummer
- US07910595B2
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