Trimethylsilyl cyanide → HCID 15176140, Verbindung
Reaktionsgleichung
C[Si]([C:5]#[N:6])(C)C.[N:7]12[CH2:15][CH:11]([CH2:12][CH2:13][CH2:14]1)[C:10](=[O:16])[CH2:9][CH2:8]2>ClCCl.[I-].[Zn+2].[I-]>[NH2:6][CH2:5][C:10]1([OH:16])[CH:11]2[CH2:15][N:7]([CH2:14][CH2:13][CH2:12]2)[CH2:8][CH2:9]1Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
Trimethylsilyl cyanide (3 ml) was added dropwise to a stirred solution of 1-azabicyclo[3.3.1]nonan-4-one (2.5 g) and zinc iodide (0.15 g) in dry dichloromethane (20 ml) and the resulting mixture was heated at reflux for 4 hours. The mixture was cooled and the solvent removed at reduced pressure; the residue was dissolved in dry tetrahydrofuran (20 ml) and cooled to 0° C. A solution of lithium aluminium hydride in tetrahydrofuran (18 ml of 1.0M soln) was then added and the resulting solution stirred overnight at room temperature. Water (0.7 ml), followed by 15% sodium hydroxide (aq) (0.7 ml) and water (2.1 ml) were then added and the precipitate removed by filtration. Evaporation of the filtrate yielded the title compound (2.2 g); δH (360 MHz, CDCl3) 1.2-1.3 (2H, m, CH2), 1.34 (1H, m, CHH), 1.41 (1H, m, CHH), 1.6 (2H, m, CH2), 1.7-1.74 (1H, m, CHH), 1.76-1.91 (2H, m, CH2), 2.11-2.16 (1H, m, CHH), 2.67-3.18 (8H, m); m/z 170 (M+).
Aufarbeitung
- temperaturethe resulting mixture was heated
- temperatureat reflux for 4 hours
- temperatureThe mixture was cooled
- customthe solvent removed at reduced pressure
- dissolutionthe residue was dissolved in dry tetrahydrofuran (20 ml)
- additionA solution of lithium aluminium hydride in tetrahydrofuran (18 ml of 1.0M soln) was then added
- additionwere then added
- customthe precipitate removed by filtration
- customEvaporation of the filtrate
Quellen und Nachweise
- ORD-Eintrag
- ord-3216517382fb49deaa2acd4da1c4f945
- Quelldatensatz
- uspto-grants-1990_07
- Patentnummer
- US04940703
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