[C:1]1([CH2:7][N:8]2[CH2:12][CH2:11][CH:10]([C:13]3[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=3)[C:16]#[N:17])[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N>[Ni].CO>[C:1]1([CH2:7][N:8]2[CH2:12][CH2:11][CH:10]([C:13]3[CH:14]=[C:15]([CH2:16][NH2:17])[CH:18]=[CH:19][CH:20]=3)[CH2:9]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1A suspension of 3-[1-(phenylmethyl)-3-pyrrolidinyl]benzonitrile (11.90 g, 45.4 mmol) and Raney nickel (5.0 g) in methanol saturated with ammonia (100 mL) was hydrogenated in a Parr shaker at 3 atm. The resulting suspension was filtered through a pad of Celite and the filtrate concentrated to give an off-green liquid. This crude product was chromatographed (silica gel, chloroform-methanol 2:1) to give the title compound (10.12 g, 84%) as a colorless oil. 1H-NMR (250 MHz, CDCl3): δ=1.68-1.75 (2H, br. s), 1.83-1.97 (1H, m), 2.27-2.41 (1H, m), 2.51 (1H, dd, J=9.0, 8.1 Hz), 2.71 (1H, td, J=8.9, 5.9 Hz), 2.80-2.90 (1H, m), 3.01-3.08 (1H, m), 3.31-3.41 (1H, m), 3.69 (2H, AB quartet, JAB =13.3 Hz), 3.84 (2H, s), 7.11-7.39 (9H, m).
Wird geladen…
