Ammonia methanol → (3S)-3-phenylcyclopentanamine
Reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:12][CH2:11][C:10](=[N:13]O)[CH2:9]2)=[CH:4][CH:3]=1.N.CO>[Ni].O>[C:5]1([C@H:8]2[CH2:12][CH2:11][CH:10]([NH2:13])[CH2:9]2)[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of Example 1C (10 g, 39.4 mmol) and 7M NH3/MeOH (100 mL) was added to Ra—Ni 2800, water slurry (40.0 g, 682 mmol) in a 50 mL pressure bottle. The mixture was stirred at room temperature for 32 hours at 30 psi. HPLC indicated complete reaction. The mixture was filtered through a nylon membrane, concentrated, and diluted with MTBE (300 mL) and 2N NaOH (150 mL). The layers were separated and the organic layer was washed with water (100 mL) and brine (50 mL), dried (Na2SO4), filtered, and concentrated to afford the title compound (5.86 g, 36.3 mmol, 92%). MS (LCMS) m/z 162 (M+H)+.