反应详情

温度

25 °C

A solution of 126 mg (0.26 mmol) N-[2-(4-benzyloxy-phenyl)-1-tert-butylcarbamoyl-ethyl]-4-tert-butyl-benzamide in 1 mL dry THF was treated via dropwise addition with 0.78 mL (0.78 mmol) of a 1.0 M solution of borane-THF complex in THF. The resulting solution was heated under reflux for 8 hours. The mixture was cooled to 25° C. and 1 mL of 5 M HCL solution was carefully added, dropwise, followed by neutralization with saturated aqueous sodium bicarbonate. The mixture was extracted with three 7 mL portions of ethyl acetate. The combined extracts were washed with two 25 mL portions brine, dried over anhydrous magnesium sulfate and concentrated to a hazy oil. The oil was purified by column chromatography on silica gel with 5:5:1 ethyl acetate: hexanes:methanol as eluant. There was obtained 58 mg (49%) of a clear, colorless oil that slowly crystallized to white, waxy crystals of title product; mp 63-65° C.

1. temperatureThe resulting solution was heated
2. temperatureunder reflux for 8 hours
3. addition1 mL of 5 M HCL solution was carefully added
4. extractionThe mixture was extracted with three 7 mL portions of ethyl acetate
5. washThe combined extracts were washed with two 25 mL portions brine
6. dry with materialdried over anhydrous magnesium sulfate
7. concentrationconcentrated to a hazy oil
8. customThe oil was purified by column chromatography on silica gel with 5:5:1 ethyl acetate
9. customThere was obtained 58 mg (49%) of a clear, colorless oil that
10. customslowly crystallized to white, waxy crystals of title product