反应详情

To a solution of methyl 5-(4-chlorobenzyl)-2-formyl-3,4-dimethylbenzoate (0.02 g) in THF (1.00 mL) was added (3S,4S)-3-aminotetrahydro-2H-pyran-4-ol (8.14 mg), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated, and the residue was diluted with methanol (1.00 mL). Sodium triacetoxyborohydride (0.02 g) was added thereto under argon atmosphere, and the mixture was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate, and the mixture was washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by reverse-phase HPLC. The fractions were combined, saturated aqueous sodium hydrogencarbonate solution was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (5.60 mg).

1. concentrationThe reaction mixture was concentrated
2. additionthe residue was diluted with methanol (1.00 mL)
3. additionSodium triacetoxyborohydride (0.02 g) was added
4. stirringunder argon atmosphere, and the mixture was stirred overnight at room temperature
5. additionThe reaction mixture was diluted with ethyl acetate
6. washthe mixture was washed with water and saturated brine
7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
8. customthe solvent was evaporated under reduced pressure
9. customThe residue was purified by reverse-phase HPLC
10. additionsaturated aqueous sodium hydrogencarbonate solution was added
11. extractionthe mixture was extracted with ethyl acetate
12. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
13. customthe solvent was evaporated under reduced pressure