反应详情

t-Butylglycinate Schiff base 3 (136 mg, 0.46 mmol) in a mixture of dry THF-DMPU 60:40 (2.5 mL) at −78° C. was treated with a 2.0 M LDA solution (0.23 mL, 0.46 mmol) and the mixture was stirred for one h at the same temperature. 2-Fluoro-5-methoxybenzyl bromide (35, 100 mg, 0.46 mmol) in dry THF (2.5 mL) was added dropwise at −78° C. and then the mixture was stirred overnight at room temperature. The reaction was quenched with saturated aqueous ammonium chloride (10 mL), and the product was extracted with diethyl ether (2×15 mL). The combined organic layers were washed with saturated aqueous ammonium chloride (4×10 mL), dried over sodium sulfate, filtered and evaporated to give 40 as a crude yellow oil (110%). When examined, the pure product 40 was made in 80% yield (175 mg).

1. stirringthe mixture was stirred overnight at room temperature
2. customThe reaction was quenched with saturated aqueous ammonium chloride (10 mL)
3. extractionthe product was extracted with diethyl ether (2×15 mL)
4. washThe combined organic layers were washed with saturated aqueous ammonium chloride (4×10 mL)
5. dry with materialdried over sodium sulfate
6. filtrationfiltered
7. customevaporated