反应详情

温度

-78 °C

A solution of 2-tert-butylcarbonylamino-4-picoline (Step A, 250 mg) in anhydrous ethyl ether (5 mL) was cooled to -78° C. and treated with tert-butyllithium (1.7 mL, 1.7 M), and stirred at -78° C. for 3 hrs. To this was added dimethyl disulfide (0. 177 mL) and the reaction was allowed to warm to room temperature. The mixture was diluted with water and ethyl ether. The aqueous layer was extracted with ether. The combined organic layers were washed with saturated sodium chloride, dried over sodium sulfate, and concentrated in vacuo. The resulting oil was purified by medium pressure liquid chromatography on a 21×300 mm silica column eluted with 40% ethyl acetate/methylene chloride to afford the title compound (260 mg, lower Rf spot) and 2-tert-butylcarbonylamino-4-methylthiomethylpyridine (40 mg, higher Rf spot).

1. temperatureto warm to room temperature
2. extractionThe aqueous layer was extracted with ether
3. washThe combined organic layers were washed with saturated sodium chloride
4. dry with materialdried over sodium sulfate
5. concentrationconcentrated in vacuo
6. customThe resulting oil was purified by medium pressure liquid chromatography on a 21×300 mm silica column
7. washeluted with 40% ethyl acetate/methylene chloride