反应详情

温度

0 °C

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+).

1. temperaturethe resulting mixture was heated
2. temperatureat reflux for 4 hours
3. temperatureThe mixture was cooled
4. customthe solvent removed at reduced pressure
5. dissolutionthe residue was dissolved in dry tetrahydrofuran (20 ml)
6. additionA solution of lithium aluminium hydride in tetrahydrofuran (18 ml of 1.0M soln) was then added
7. additionwere then added
8. customthe precipitate removed by filtration
9. customEvaporation of the filtrate