Reaktionsgleichung
Cl.[NH2:2][C:3]12[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][C:5]([C:13]([OH:15])=[O:14])([CH2:6]3)[CH2:4]1)[CH2:10]2.S(Cl)([Cl:18])=O.[CH3:20]O>>[ClH:18].[CH3:20][O:14][C:13]([C:5]12[CH2:11][CH:9]3[CH2:8][CH:7]([CH2:12][C:3]([NH2:2])([CH2:10]3)[CH2:4]1)[CH2:6]2)=[O:15]Komponenten
Reaktionsbedingungen
- Temperatur
- 60 °C
Versuchsvorschrift
To a 3-neck 2-L flask equipped with a reflux condenser and a temperature probe was added 3-amino-adamantane-1-carboxylic acid hydrochloride (100 g, 432 mmol) and methanol (1.0 L). To this solution was slowly added thionyl chloride (15.7 mL, 216 mmol) and the reaction was heated at 60° C. for 4 hours. Once cooled to room temperature, the crude reaction mixture was concentrated under reduced pressure to remove most of the methanol. Heptane (about 1-L) was then added and the mixture was once again concentrated under reduced pressure at which point a solid began to precipitate. This process was repeated three more times, then the solids were filtered off, washed with heptane and allowed to dry in open air to afford 97.2 g (92%) of the title compound, 3-amino-adamantane-1-carboxylic acid methyl ester hydrochloride, as a white solid. 1H NMR (300 MHz, CDCl3) δ 8.46 (br s, 3H), 3.65 (s, 3H), 2.33-2.24 (m, 2H), 2.23-2.16 (m, 2H), 2.11-1.95 (m, 4H), 1.94-1.78 (m, 4H), 1.75-1.62 (m, 2H).
Aufarbeitung
- temperatureOnce cooled to room temperature
- customthe crude reaction mixture
- concentrationwas concentrated under reduced pressure
- customto remove most of the methanol
- additionHeptane (about 1-L) was then added
- concentrationthe mixture was once again concentrated under reduced pressure at which point a solid
- customto precipitate
- filtrationthe solids were filtered off
- washwashed with heptane
- customto dry in open air
Quellen und Nachweise
- ORD-Eintrag
- ord-9ec47c4cf75c4e27b8c7d5ba57be580d
- Quelldatensatz
- uspto-grants-2012_06
- Patentnummer
- US08198275B2
Verknüpfte Notizen
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