Borane → 1,1-Dimethylethyl 4-{[3'-(aminomethyl)-3-biphenylyl]methyl}-1-piperazinecarboxylate

Participants

Reaction Steps

A solution of 1,1-dimethylethyl 4-[(3′-cyano-3-biphenylyl)methyl]-1-piperazinecarboxylate (4.5 g) in THF (30 mL) was treated with borane. THF (47.7 mL, 1M in THF) and the resulting mixture was heated at reflux for 1 hour. After cooling to room temperature, the reaction mixture was quenched with saturated ammonium chloride solution (20 mL) and extracted with ethyl acetate (3×30 mL). The combined organics were dried (MgSO4), concentrated under vacuum to give a residue which was purified by flash chromatography on silica (100 g) to yield the title compound (1.1 g). LC/MS: m/z, 382 (M+H), 1.86 min.

Provenance & Evidence