反応 #12014
ord-90af6704e9c3417f9f4a191d574bb4d4
反応方程式
反応物
反応条件
後処理
- 1温度was heated
- 2温度to reflux for 2 h
- 3workup.ADDITIONwas added
- 4温度The mixture was heated
- 5温度to reflux for 16 h
- 6温度then cooled to room temperature
- 7その他the phases were separated
- 8抽出The aqueous phase was extracted three times with ethyl acetate
- 9洗浄the combined organic layers were washed with 1M aqueous sodium hydroxide solution and brine
- 10乾燥dried over magnesium sulfate
- 11ろ過filtered
- 12その他evaporated
- 13その他The residue was purified by chromatography on silica gel (0.032–0.063 mm) with n-hexane as eluant
実験手順
A suspension of 150.0 mg (1.23 mmol) 9-borabicyclo[3.3.1]nonane and 47 μl (0.62 mmol) propargyl bromide in 1 ml tetrahydrofuran was heated to reflux for 2 h. The mixture was cooled to room temperature then 0.61 ml (1.83 mmol) of a degassed 3M sodium hydroxide solution was added and after 1 h a mixture of 0.20 g (0.54 mmol) (4R,9aR)-6-bromo-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester (Example 5, intermediate b) and 19.0 mg tetrakis(triphenylphosphine)palladium in 1 ml tetrahydrofuran was added. The mixture was heated to reflux for 16 h then cooled to room temperature and poured into water and ethyl acetate; the phases were separated. The aqueous phase was extracted three times with ethyl acetate and the combined organic layers were washed with 1M aqueous sodium hydroxide solution and brine, dried over magnesium sulfate, filtered and evaporated. The residue was purified by chromatography on silica gel (0.032–0.063 mm) with n-hexane as eluant to afford the desired product as a colorless oil (35.2%).