反应详情

Cyclopropylamine (1.04 mL, 14.92 mmol, 5 equiv.) was added to a solution of 3-(3-(neopentylamino)benzo[d]isoxazol-5-yl)benzaldehyde (exemplary compound 52) (0.92 g, 2.98 mmol, 1 equiv.) in THF (50 mL) and sodium cyanoboran hydride (3.16 g, 14.92 mmol, 5 equiv.) was subsequently added to the mixture. The suspension was stirred for 3 days at RT, subsequently hydrolysed by the addition of sat. aq. sodium hydrogen carbonate sol. (approx. 5 mL) and the solvent removed in a vacuum. The residue was absorbed in EtOAc (10 mL) and extracted with sat. aq. sodium hydrogen carbonate sol. (2×15 mL) and sat. aq. NaCl solution (1×15 mL), dried (MgSO4) and the solvent removed in a vacuum. After column-chromatographic purification (EtOAc/MeOH; 20:1), the desired product (0.85 g, 82%) is obtained.

1. additionwas subsequently added to the mixture
2. customthe solvent removed in a vacuum
3. customThe residue was absorbed in EtOAc (10 mL)
4. extractionextracted with sat. aq. sodium hydrogen carbonate sol. (2×15 mL) and sat. aq. NaCl solution (1×15 mL)
5. dry with materialdried (MgSO4)
6. customthe solvent removed in a vacuum
7. customAfter column-chromatographic purification (EtOAc/MeOH; 20:1)