Cyclopropylamine → 5-(3-((cyclopropylamino)methyl)phenyl)-N-neopentylbenzo[d]isoxazol-3-amine

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Reaction Steps

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.

Provenance & Evidence