(S)-2-((1-butyrylpiperidin-3-yl)methoxy)-6-nitrobenzonitrile → (S)-2-amino-6-((1-butyrylpiperidin-3-yl)methoxy)benzonitrile

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-2-((1-butyrylpiperidin-3-yl)methoxy)-6-nitrobenzonitrile (Example 1c, 9.92 g, 32.92 mmol) in acetic acid (60 mL) and THF (60 mL), was added iron powder (5.5 g, 98.76 mmol) at room temperature. The reaction mixture was heated to 70° C. and stirred for 1 hour then cooled to room temperature, diluted with EtOAc, filtered through Celite. The filtrate was concentrated under reduced pressure and then re-dissolved in EtOAc, washed with NaHCO3, water and brine, dried over MgSO4, filtered and evaporated. The residue was crystallized from DCM/EtOAc, to give the title compound as off white solid (9.92 g, 93% for 2 steps). MS 302 (MH+).

Provenance & Evidence