反应详情

温度

-78 °C

Tert-butyl[(tert-butoxycarbonyl)amino]acetate (1.01 g, 4.37 mmol) was dissolved in THF (10 mL) and cooled to −78° C. LiHMDS (6.5 mL, 1M solution in THF) was slowly added and allowed to stir for 30 minutes. Methyl 4-(bromomethyl)benzoate (1.98 g, 8.64 mmol) in THF (6 mL) was added to the mixture and allowed to stir overnight, slowly warming to room temperature. The reaction was diluted with ethyl acetate and quenched with saturated ammonium chloride. The aqueous layer was extracted three times with ethyl acetate. The combined organic layer was dried over sodium sulfate, filtered, and concentrated. The resulting residue was purified by column chromatography. MS: cal'd 379 (MH+), exp 402 (MH+).

1. stirringto stir overnight
2. temperatureslowly warming to room temperature
3. customquenched with saturated ammonium chloride
4. extractionThe aqueous layer was extracted three times with ethyl acetate
5. dry with materialThe combined organic layer was dried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated
8. customThe resulting residue was purified by column chromatography