Ammonium Acetate → (5S,6S,9R)-5-Azido-6-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-9-amine

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Reaction Steps

To a solution of (5S,6S)-5-azido-6-(2,3-difluorophenyl)-5,6,7,8-tetrahydro-9H-cyclohepta[b]pyridin-9-one (190 mg, 0.60 mmol), and ammonium acetate (2.3 g, 30 mmol) in MeOH (10 mL) was added sodium cyanoborohydride (27 mg, 0.42 mmol) and the resulting mixture was stirred at ambient temperature for 16 h. The reaction mixture was concentrated under reduced pressure and the residue was partitioned between dichloromethane (20 mL) and aqueous 1 N NaOH solution (5 mL). The organic layer was separated, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography, eluting with a gradient of EtOAc:MeOH:Et3N-100:0:0 to 85:10:5, to give the title compound as a mixture of diastereomers. MS: m/z=316.2 (M+1).

Provenance & Evidence