反应详情

温度

-78 °C

In tetrahydrofuran (15 ml) were dissolved N-tert-butoxycarbonyl-5-bromo-1,2,3,4-tetrahydroisoquinoline (0.9 g) and N-methyl-N-methyloxy-2-amino-5-chlorobenzamide (0.68 g). The solution was cooled to −78° C., to which was added dropwise, while stirring, n-butyl lithium (1.6 mol, hexane solution) (9 ml) over 30 minutes. To the reaction mixture was added water (50 ml) to decompose, followed by extraction with ethyl acetate (80 ml). The organic layer was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by means of a silica gel column chromatography to give 2-(N-tert-butoxycarbonyl-1,2,3,4-tetrahydroisoquinolin-5-yl)carbonyl-4-chloro-aniline (0.26 g) as a yellow crystalline product. m.p.: 159-160° C.

1. additionwas added dropwise
2. extractionfollowed by extraction with ethyl acetate (80 ml)
3. washThe organic layer was washed with water
4. dry with materialdried over anhydrous sodium sulfate
5. distillationThe solvent was distilled off
6. customthe residue was purified by means of a silica gel column chromatography