反应详情

To a solution of 2-ethyl-3-{5-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,3,4-thiadiazol-2-yl}benzaldehyde (D6) (54 mg) and ethyl 4-piperidinecarboxylate (101 mg) in ethanol (10 mL) stirred at room temperature was added AcOH (0.037 mL). The reaction mixture was stirred at room temperature for 10 min. Then the solvent was removed by evaporation. To the residue was added dichloromethane (DCM) (10 mL) and sodium triacetoxyborohydride (82 mg). Stirring continued for 2 h. Water was added to quench the reaction, and DCM was removed by evaporation. The mixture was extracted by EA for 3 times. The combined organic phases were washed by brine, dried over anhydrous Na2SO4. The dried solution was filtered and concentrated to afford the crude product ethyl 1-[(2-ethyl-3-{5-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,3,4-thiadiazol-2-yl}phenyl)methyl]-4-piperidinecarboxylate (D7) (72.1 mg). MS (ES): C29H34F3N3O3S requires 561. found 562.1 (M+H+).

1. customThen the solvent was removed by evaporation
2. additionTo the residue was added dichloromethane (DCM) (10 mL) and sodium triacetoxyborohydride (82 mg)
3. stirringStirring
4. waitcontinued for 2 h
5. additionWater was added
6. customto quench
7. customthe reaction, and DCM
8. customwas removed by evaporation
9. extractionThe mixture was extracted by EA for 3 times
10. washThe combined organic phases were washed by brine
11. dry with materialdried over anhydrous Na2SO4
12. filtrationThe dried solution was filtered
13. concentrationconcentrated