[CH2:1]([N:3]([CH2:11][CH3:12])[C:4]1([C:9]#[N:10])[CH2:8][CH2:7][CH2:6][CH2:5]1)[CH3:2].[C:13]1([Li])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[BH4-].[Na+].NC(C1C=CC=CC=1)C1(N(C)C)CCCC1>C(OCCCC)CCC.C1COCC1.CO>[NH2:10][CH:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:4]1([N:3]([CH2:1][CH3:2])[CH2:11][CH3:12])[CH2:5][CH2:6][CH2:7][CH2:8]1
The title compound (0.45 g, 47%) was prepared from 1-(diethylamino)cyclopentane carbonitrile D11 (0.65 g, 3.9 mmol), and phenyllithium in dibutylether (2.4 ml of a 1.8M solution; 4.3 mmol) in THF (4 ml), followed by reaction with sodium borohydride (0.445 g, 11.7 mmol) in methanol (4 ml) in a similar manner to that described in D2. 1H NMR (CDCl3) δ: 0.42 (1H, m), 1.10 (6H, m), 1.35 (3H, m), 1.55 (1H, m), 1.66 (2H, m), 1.80-2.08 (3H, m), 2.53-2.70 (4H, m), 4.22 (1H, s), 7.20-7.31 (3H, m), 7.47 (2H, m).
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