反应详情

温度

0 °C

Benzyl glyoxylate (3.28 g, 20.0 mmol) in dry tetrahydrofuran (15 ml) was added dropwise in monoacetylethylenediamine (1.53 g, 15 mmol) in dry tetrahydrofuran (60 ml) at room temperature. After 2 hours, the tetrahydrofuran was removed under vacuum, and the residue was dissolved in dry methanol (100 ml). Upon cooling to 0° C., 1.55 g of sodium cyanoborohydride was added, immediately followed by dropwise addition of 1.54 ml of acetic acid. The reaction was allowed to warm to room temperature and stirred for 40 minutes. The volatiles were removed under vacuum, and the residue was extracted from aqueous sodium bicarbonate with ethyl acetate. The combined organic layers were dried with sodium sulfate, and the volatiles were removed. The residue was purified by column chromatography on silica (LPS-1) (loading with 2% methanol/dichloromethane and eluting with 5% methanol/dichloromethane to yield 1.46 g of the title compound.

1. customthe tetrahydrofuran was removed under vacuum
2. dissolutionthe residue was dissolved in dry methanol (100 ml)
3. addition1.55 g of sodium cyanoborohydride was added
4. additionimmediately followed by dropwise addition of 1.54 ml of acetic acid
5. temperatureto warm to room temperature
6. customThe volatiles were removed under vacuum
7. extractionthe residue was extracted from aqueous sodium bicarbonate with ethyl acetate
8. dry with materialThe combined organic layers were dried with sodium sulfate
9. customthe volatiles were removed
10. customThe residue was purified by column chromatography on silica (LPS-1) (loading with 2% methanol/dichloromethane
11. washeluting with 5% methanol/dichloromethane