4-Aminomethyl-1-N-Cbz-piperidine → Benzyl 4-((2-hydroxy-3-((oxoboryl)methyleneamino)-4-phenylbutylamino)methyl)piperidine-1-carboxylate

Participants

Reaction Steps

1-(oxiran-2-yl)-N-((oxoboryl)methylene)-2-phenylethanamine (1.61 mmol, 424 mg) and benzyl 4-(aminomethyl)piperidine-1-carboxylate (1.94 nmnol, 480 mg) in isopropanol (20 mL) was heated at 80° C. for overnight. Evaporated the solvent and purified by flash chromatography to get benzyl 4-((2-hydroxy-3-((oxoboryl)methyleneamino)-4-phenylbutylamino)methyl)piperidine-1-carboxylate (880 mg). 1H NMR (300 MHz, CDCl3), δ: 7.363-7.174 (m, 10H), 5.118 (s, 2H), 4.767 (br, 1H), 4.187 (m, 2H), 3.786 (m, 1H), 3.458 (m, 1H), 3.023-2.671 (m, 6H), 2.484 (d, J=6.6 Hz, 2H), 1.733 (m, 2H), 1.600 (m, 1H), 1.347 (s, 9H), 1.135 (m, 2H).

Provenance & Evidence