benzyl [(3S,7S)-1-methyl-2-oxo-7-phenyl-2,3,4,7-tetrahydro-1H-azepin-3-yl]carbamate → (3S,7S)-3-amino-1-methyl-7-phenylazepan-2-one

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Reaction Steps

A mixture of benzyl [(3S,7S)-1-methyl-2-oxo-7-phenyl-2,3,4,7-tetrahydro-1H-azepin-3-yl]carbamate (2c) (216 mg) and Pearlman's catalyst (40 mg) in EtOH (7 mL) was hydrogenated at 45 psi overnight. The reaction mixture was filtered through Celite and concentrated in vacuo. The residue was dissolved in EtOAc and washed with saturated NaHCO3, brine, dried (Na2SO4), filtered and concentrated to a viscous oil. The aqueous layer from above were extracted 3×50 ml DCM. The combined organic layer was washed with brine, dried (Na2SO4), filtered and concentrated to a viscous oil (60 mg). The two isolated oils were combined to give a 90% yield of the desired product. 1H NMR (300 MHz, CDCl3) δ 1.57-2.12 (m, 9H), 2.53 (s, 3H), 4.92 (d, 1H), 7.26-7.41 (m, 5H). APCI, m/z=219 (M+1). LC/MS 1.82 min., Method A

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