反应详情

Preparation 1-B: A solution of hydrogen chloride in 1,4-dioxane (4 M, 60 mL, 240 mmol) was added to tert-butyl 4-[2-azido-1-(4-bromophenyl)ethyl]piperidinecarboxylate 13 (2.5 g, 6.1 mmol). The reaction mixture was stirred at room temperature for 1 h. The solvent was evaporated under reduced pressure. The residue containing 4-[2-azido-1-(4-bromophenyl)ethyl]piperidine hydrochloride 14 was dissolved in a 50% v/v aqueous tetrahydrofuran solution (68 mL). Potassium carbonate (2.12 g, 15.3 mmol) and 2-(trimethylsilyl)ethyl p-nitrophenyl carbonate (1.74 g, 61.4 mmol) were added. The reaction mixture was stirred at room temperature for 3 h. Organic solvent was evaporated under reduced pressure. Ethyl acetate was added. The organic layer was washed with aqueous sodium bicarbonate solution, water and brine. The organic layer was dried over sodium sulfate. The solvent was evaporated under reduced pressure. The crude product was purified by flash column chromatography eluted with ethyl acetate-hexanes (1:5 v/v) to afford 2-(trimethylsilyl)ethyl 4-[2-azido-1-(4-bromophenyl)ethyl]piperidinecarboxylate 15 (2.1 g, 4.6 mmol). MS (LCMS-Electrospray) 454.1 MH+.

1. customThe solvent was evaporated under reduced pressure
2. additionThe residue containing 4-[2-azido-1-(4-bromophenyl)ethyl]piperidine hydrochloride 14
3. dissolutionwas dissolved in a 50% v/v aqueous tetrahydrofuran solution (68 mL)
4. stirringThe reaction mixture was stirred at room temperature for 3 h
5. customOrganic solvent was evaporated under reduced pressure
6. additionEthyl acetate was added
7. washThe organic layer was washed with aqueous sodium bicarbonate solution, water and brine
8. dry with materialThe organic layer was dried over sodium sulfate
9. customThe solvent was evaporated under reduced pressure
10. customThe crude product was purified by flash column chromatography
11. washeluted with ethyl acetate-hexanes (1:5 v/v)