Borane → 1,1-Dimethylethyl (2S)-4-{[3'-(aminomethyl)-4'-fluoro-3-biphenylyl]methyl}-2-methyl-1-piperazinecarboxylate

Participants

Reaction Steps

A solution of 1,1-dimethylethyl (2S)-4-[(3′-cyano-4′-fluoro-3-biphenylyl)methyl]-2-methyl-1-piperazinecarboxylate (2.29 g, 5.59 mmol) in THF (50 mL) was flushed with Ar. Borane (19 mL, 1M in THF, 19 mmol) was slowly added and the reaction was allowed to stir at room temperature for 12 hours. The reaction was quenched slowly with water, diluted with water (175 mL) and then extracted with EtOAc (2×250 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated under vacuum. The crude residue was placed onto a SPE silica cartridge (20 g) using 50% hexane/50% EtOAc, and then eluted with the following sequence: 50% hexane/50% EtOAc, 10% MeOH/90% DCM, 30% MeOH/70% DCM. The product fractions were combined and concentrated to give the title compound (1.48 g, 64.1%). EI-MS m/z 414(M−H)+.

Provenance & Evidence