反应详情

温度

0 °C

Borane tetrahydrofuran complex (1M, 2.8 mL, 2.8 mmol) was added drop wise to a solution of di-tert-butyl 4-allyl-N-trityl-L-glutamate (1.00 g, 1.85 mmol) in THF (10 mL) at 0° C. The resulting mixture was stirred for 2 h at 0° C. and for 16 h at room temperature. The solution was cooled to 0° C. NaOH (1M, 3 mL) and H2O2 (30% in water, 3 mL) were added drop wise. The mixture was stirred at 0° C. for 1 h. Water (5 mL) was added and the mixture was concentrated under reduced pressure. The aqueous residue was extracted with ethyl acetate. The combined organic fraction was washed with brine, dried over sodium sulfate, filtrated and concentrated. The crude product was purified by flash chromatography (silica, ethyl acetate/hexane) to afford di-tert-butyl 4-(3-hydroxypropyl)-N-trityl-L-glutamate (0.46 g, 44%) as a mixture of (4S,4S)/(2S,4R) diastereoisomers.

1. temperatureThe solution was cooled to 0° C
2. stirringThe mixture was stirred at 0° C. for 1 h
3. concentrationthe mixture was concentrated under reduced pressure
4. extractionThe aqueous residue was extracted with ethyl acetate
5. washThe combined organic fraction was washed with brine
6. dry with materialdried over sodium sulfate
7. filtrationfiltrated
8. concentrationconcentrated
9. customThe crude product was purified by flash chromatography (silica, ethyl acetate/hexane)