Hydrazine hydrate (1:1) → (3S,7S)-3-amino-1-benzyl-7-phenyl-1,3,4,7-tetrahydro-2H-azepin-2-one

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Reaction Steps

To 2-[(7S)-1-benzyl-2-oxo-7-phenyl-2,3,4,7-tetrahydro-1H-azepin-3-yl]-1H-isoindole-1,3(2H)-dione (5c) (126 mg) dissolved in MeOH (4 mL) was added hydrazine hydrate (0.036 mL) and the mixture was stirred overnight at RT. A white precipitate formed in solution. The reaction mixture was diluted with ether and the precipitate was filtered and washed with ether. The etheral filtrate was concentrated and the resulting residue dissolved in DCM. The DCM solution was washed with H2O and brine, dried (Na2SO4) and concentrated. The diastereomeric mixture was separated via preparative plate chromatography (eluent 10% MeOH/DCM) to give (3R,7S)-3-amino-1-benzyl-7-phenyl-1,3,4,7-tetrahydro-2H-azepin-2-one (5e) and (3S,7S)-3-amino-1-benzyl-7-phenyl-1,3,4,7-tetrahydro-2H-azepin-2-one (5d) (combined yield of 72%).

Provenance & Evidence