反应详情

温度

-40 °C

In a 25 ml flask 4-(t-butoxycarbonylamino)butanol was dissolved in tetrahydrofuran (15 ml) under a nitrogen atmosphere. The solution was cooled to −40° C. and potassium tert-butoxide (1M in tetrahydrofuran, 2.14 ml, 2.14 mmol) was added slowly. The resulting mixture was stirred at −40° C. for thirty minutes. To this reaction mixture was added 2-fluoro-5-bromobenzyl bromide (521 mg, 1.94 mmol), added dropwise as a solution in tetrahydrofuran (3.5 ml). The resulting mixture was slowly warmed to 0° C. and stirred at this temperature for two hours. The progress of the reaction was monitored by thin layer chromatography. The reaction mixture was partitioned between 1 M potassium carbonate and methylene chloride. The aqueous fraction was back-extracted with methylene chloride. The organic fractions were combined and dried over sodium sulfate. The solvents were removed in vacuo. The desired intermediate was further purified by liquid chromatography.

1. temperatureThe resulting mixture was slowly warmed to 0° C.
2. stirringstirred at this temperature for two hours
3. customThe reaction mixture was partitioned between 1 M potassium carbonate and methylene chloride
4. extractionThe aqueous fraction was back-extracted with methylene chloride
5. dry with materialdried over sodium sulfate
6. customThe solvents were removed in vacuo
7. customThe desired intermediate was further purified by liquid chromatography