反应详情

温度

-30 °C

To a solution of tert-butyl 4-(1,2-dihydro-5-acenaphthylenyl)-4-hydroxy-1-piperidinecarboxylate (0.44 g, 1.24 mmol) in dichloromethane (4 mL) was added triethylsilane (1.10 mL, 6.22 mmol) under nitrogen. The mixture was cooled to −30° C. then trifluoroacetic acid (0.48 mL, 6.22 mmol) added dropwise, maintaining the temperature below −25° C. After 2.5 h, the reaction mixture was allowed to warm to 0° C. and additional trifluoroacetic acid (0.48 mL, 6.22 mmol) added over 5 min. The reaction mixture was allowed to warm to room temperature and left to stir for 3 days. Ice was then added to the reaction mixture, followed by potassium hydroxide to a pH of 14, and the resultant slurry extracted with dichloromethane. The combined organic extracts were dried (Na2SO4) and concentrated in vacuo to yield a yellow oil. The oil was dissolved in methanol and loaded onto an SCX-2 column. The column was washed with methanol, then a 2N solution of ammonia in methanol. Concentration in vacuo of the ammonia solution yielded 4-(1,2-dihydro-5-acenaphthylenyl)piperidine as a pale yellow oil.

1. temperaturemaintaining the temperature below −25° C
2. temperatureto warm to 0° C.
3. temperatureto warm to room temperature
4. waitleft
5. additionIce was then added to the reaction mixture
6. extractionthe resultant slurry extracted with dichloromethane
7. dry with materialThe combined organic extracts were dried (Na2SO4)
8. concentrationconcentrated in vacuo
9. customto yield a yellow oil
10. washThe column was washed with methanol
11. concentrationConcentration in vacuo of the ammonia solution