反应详情

温度

4 °C

2-Bromothiazole (0.500 g, 3.05 mmol) was dissolved in anhydrous THF (7.62 mL) and cooled to 4° C. (ice bath) under nitrogen. i-PrMgCl.LiCl in THF (2.0 M, 1.52 mL, 3.05 mmol) was added and the reaction stirred at this temperature for 30 minutes. The ice bath was removed and the reaction stirred for 30 minutes at room temperature. (2R,5R)-2-Formyl-5-methyl-piperazine-1,4-dicarboxylic acid di-tert-butyl ester (0.500 g, 1.52 mmol) was added and the reaction stirred for 2 h. The reaction mixture was quenched with water and extracted with DCM (3×). The combined organic extracts were dried with sodium sulfate, filtered and concentrated. Chromatography (silica gel, gradient elution, 0-100%, EtOAc in petrol 40-60) gave the title compound (473 mg). MS: [M+H]+=414.

1. customThe ice bath was removed
2. stirringthe reaction stirred for 30 minutes at room temperature
3. stirringthe reaction stirred for 2 h
4. customThe reaction mixture was quenched with water
5. extractionextracted with DCM (3×)
6. dry with materialThe combined organic extracts were dried with sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated
9. washChromatography (silica gel, gradient elution, 0-100%, EtOAc in petrol 40-60)