tert-Butyl (3-aminopropyl)carbamate → (3-{3-[3-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-ureido}-propyl)-carbamic acid tert-butyl ester

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Reaction Steps

(3-Amino-propyl)-carbamic acid tert-butyl ester (0.79 ml, 4.5 mmol) was added slowly to a stirred solution of 2-(3-isocyanato-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (1 g, 4.1 mmol) in dry THF (8 ml) at RT under N2 After 16 hours the volatiles were removed in vacuo and the residue was partitioned between EtOAc/H2O. The organic layer was washed with brine (×1), then dried (Na2SO4), filtered and evaporated to give the title compound (1.6 g) as a colourless solid. 1H NMR (400 MHz, DMSO-d6): 8.52 (1H, s), 7.77 (1H, s), 7.47 (1H, dt), 7.25-7.17 (2H, m), 6.80 (1H, t), 6.08 (1H, t), 3.13-3.02 (2H, m), 3.02-2.89 (2H, m), 1.57-1.48 (2H, m), 1.39 (9H, s), 1.29 (12H, s).

Provenance & Evidence