Acetic Acid → 3-{[4-(BOC-methyl-amino)-cyclohexylamino]-methyl}-4-fluoro-benzene boronic acid

Participants

Reaction Steps

To a solution of 4-fluoro-3-formyl benzene boronic acid (0.88 g, 5.99 mmol) in THF (5 mL) and toluene (5 mL) was added amine (3) (1.4 g, 7.19 mmol) followed by AcOH (0.34 mL, 7.19 mmol), and the resulting solution was stirred at RT for 18 h. After this time sodium triacetoxyborohydride (1.57 g, 8.38 mmol) was added and the resulting solution was stirred at RT for a further 6 h. EtOAc (10 mL) was added to the reaction mixture followed by dropwise addition of sat. NaHCO3 solution (10 mL). The organic layer was separated and the aqueous layer was extracted into EtOAc (2×10 mL). The combined organic layers were dried (MgSO4), filtered and reduced in vacuo to give the title compound as a yellow solid.

Provenance & Evidence