[C:1]1([C@@H:7]2[CH2:11][N:10]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:9][C@H:8]2[C:19]#[N:20])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[C:1]1([CH:7]2[CH2:11][N:10]([CH2:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:9][CH:8]2[CH2:19][NH2:20])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1To a solution of 5.7 g (0.022 mole) of trans-4 -phenyl-1-(phenylmethyl)-3-pyrrolidinecarbonitrile (Helv. Chim. Acta, 64, 2203 (1981)) in 30 ml tetrahydrofuran was added 0.83 g (0.022 mmol) of lithium aluminum hydride in portions under nitrogen. The reaction mixture was then stirred at room temperature for 18 hours. To the resulting suspension were added 1 ml of water, 0.8 ml of 40% sodium hydroxide, and 3 ml of water. The grainy precipitate was filtered and washed with tetrahydrofuran. The combined filtrates were concentrated to give 5.5 g of 4-phenyl-1-(phenylmethyl)-3-pyrrolidinemethanamine.
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