반응 #12014
ord-90af6704e9c3417f9f4a191d574bb4d4
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후처리
- 1온도was heated
- 2온도to reflux for 2 h
- 3workup.ADDITIONwas added
- 4온도The mixture was heated
- 5온도to reflux for 16 h
- 6온도then cooled to room temperature
- 7기타the phases were separated
- 8추출The aqueous phase was extracted three times with ethyl acetate
- 9세척the combined organic layers were washed with 1M aqueous sodium hydroxide solution and brine
- 10건조dried over magnesium sulfate
- 11여과filtered
- 12기타evaporated
- 13기타The residue was purified by chromatography on silica gel (0.032–0.063 mm) with n-hexane as eluant
실험 절차
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%).