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. Author manuscript; available in PMC: 2016 Aug 10.
Published in final edited form as: J Med Chem. 2016 Apr 4;59(7):3471–3488. doi: 10.1021/acs.jmedchem.6b00085

Scheme 3. Synthesis of Amines from Aromatic Aldehydesa.

Scheme 3

aConditions: (a) HNO3, H2SO4, Ac2O, 0 °C, 1 h; (b) 50% H2SO4 (aq), 110 °C, 5 min; (c) conc HCl, 40 °C, 12 h; (d) NH2OH·HCl, NaOAc, MeOH, 25 °C, 8 h; (e) LiAlH4, THF, 0–25 °C, 12 h; (f) potassium vinyltrifluoroborate, Pd(dppf)Cl2, iPr2EtN, toluene, 110 °C, 14 h; (g) H2, 10% Pd/C, EtOH, 25 °C, 6 h.