tert-Butyl (1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)methylcarbamate → 6-(aminomethyl)benzo[c][1,2]oxaborol-1(3H)-ol

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Reaction Steps

tert-Butyl (1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)methylcarbamate (CXI) (0.27 g, 1.02 mmol) was dissolved in HCl/EtOAc (4.2 M, 7 mL/mmol) and stirred for 30 minutes at room temperature. The solvent was removed under vacuum and residue was triturated with Et2O to give 6-(aminomethyl)benzo[c][1,2]oxaborol-1(3H)-ol (CXII) as a white solid (0.15 g, 0.75 mmol, 74% yield). 1H NMR (DMSO-d6) δ ppm 4.00 (s, 2H), 4.69 (s, 2H), 7.21-7.51 (brs, 1H), 7.52-7.66 (brs, 1H), 7.67-7.88 (brs, 1H), 8.06-8.98 (brs, 3H); ESIMS found for C8H10BNO2 m/z 146.7 (M−H2O+1).

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