反应详情

In an atmosphere of argon gas, 1M solution of diisobutylaluminum hydride in toluene (2.7 ml, 2.7 mmoles) was slowly added at -78° C. to solution of (2S,3S)-2,3-bis-(t-butyldiphenylsilyloxymethyl)-1-cyclopentanone (1.40 g, 2.25 mmoles) in toluene (23 ml), and the resulting mixture was stirred at that temperature for 15 minutes. Then, 0.2M phosphate buffer solution (pH 7) was added to the reaction mixture and stirred for a while, after which an excessive amount of methylene chloride was added and the inorganic matter was filtered off. The filtrate was subjected to extraction with methylene chloride and an extract solution was dried on anhydrous sodium sulfate, and then the solvent was distilled off. The residue was purified by silica gel column chromatography (ethyl acetate: n-hexane=1:10, v/v) to obtain (1S,2S,3S)-2,3-bis(t-butyldiphenylsilyloxymethyl)-1-cyclopentanol (1,120 g, Yield 80%):

1. stirringstirred for a while
2. filtrationthe inorganic matter was filtered off
3. extractionThe filtrate was subjected to extraction with methylene chloride
4. dry with materialan extract solution was dried on anhydrous sodium sulfate
5. distillationthe solvent was distilled off
6. customThe residue was purified by silica gel column chromatography (ethyl acetate