反应详情

温度

-95 °C

2-Fluoro-5-iodo-3-methylpyridine (200 mg, 0.84 mmol) was dissolved in Et2O and cooled to -95° C. A solution of 2.5M t-BuLi (1.7M in pentane, 1.1 mL, 1.80 mmol) in pentane was added dropwise. 1,2,3,5,6,7-hexahydropyrrolizinium perchlorate (265 mg, 1.26 mmol) was added, and the reaction mixture was allowed to warm to -10° C. with stirring for 2 hours. The cold bath was removed, 2N HCl was added, and the phases were separated. The aqueous phase was basified with 15% NaOH and extracted with CH2Cl2 (2×). The CH2Cl2 fractions were combined, dried (MgSO4) and concentrated, and the residue was chromatographed (silica gel; CHCl3 /MeOH, 99:1) to afford the title compound as an oil (123 mg, 67%) 1H NMR (CDCl3, 300 MHz) δ1.55-1.71 (m, 2H), 1.78-2.04 (m, 6H), 2.26 (s, 3H), 2.64-2.72 (m, 2H), 3.11-3.18 (m, 2H), 7.70 (m, 1H), 8.09 (m, 1H); MS (CI/NH3) m/z: 221 (M+H)+.

1. temperatureto warm to -10° C.
2. customThe cold bath was removed
3. addition2N HCl was added
4. customthe phases were separated
5. extractionextracted with CH2Cl2 (2×)
6. dry with materialdried (MgSO4)
7. concentrationconcentrated
8. customthe residue was chromatographed (silica gel; CHCl3 /MeOH, 99:1)