反应详情

温度

0 °C

A solution of sodium hydride (0.16 g, 3.9 mmol) in tetrahydrofuran (10 mL) at 0° C. was treated with a solution of tert-butyl 4-(2-hydroxyethyl)piperidine-1-carboxylate (0.82 mL, 3.7 mmol) in tetrahydrofuran (5 mL) and stirred at 0° C. for 30 minutes. The reaction mixture was treated with a solution of 1-fluoro-2-iodo-4-nitrobenzene (1.0 g, 3.7 mmol) in tetrahydrofuran (5 mL) and heated at 70° C. for 16 h. The reaction mixture was concentrated, diluted with ethyl acetate, and washed with water. The aqueous layer was separated and extracted with additional ethyl acetate. The combined organic extracts were washed with brine, dried with sodium sulfate, filtered, and concentrated to a crude brown oil. Purification by flash column chromatography gave the desired product (1.4 g, 81%) as a yellow oil. LCMS for C18H251N2O5Na (M+Na)+: m/z=499.0.

1. temperatureheated at 70° C. for 16 h
2. concentrationThe reaction mixture was concentrated
3. additiondiluted with ethyl acetate
4. washwashed with water
5. customThe aqueous layer was separated
6. extractionextracted with additional ethyl acetate
7. washThe combined organic extracts were washed with brine
8. dry with materialdried with sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated to a crude brown oil
11. customPurification by flash column chromatography