[CH:1]12[CH2:6][CH:5]1[CH2:4][N:3]([C:7]([CH3:11])([CH3:10])[C:8]#[N:9])[CH2:2]2.[C:12]1([Li])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[BH4-].[Na+].NC(C1C=CC=CC=1)C1(N(C)C)CCCC1>C(OCCCC)CCC.C1COCC1.CO>[CH:5]12[CH2:6][CH:1]1[CH2:2][N:3]([C:7]([CH3:11])([CH3:10])[CH:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[NH2:9])[CH2:4]2
The title compound (393 mg, 44%) was prepared from 2-(3-azabicyclo[3.1.0]hex-3-yl)-2-methylpropanenitrile D15 (583 mg, 3.9 mmol), and phenyllithium in dibutylether (2.15 ml of a 2.0M solution; 4.3 mmol) in THF (7 ml), followed by reaction with sodium borohydride (445 mg, 11.7 mmol) in methanol (10 ml) in a similar manner to that described in D2. 1H NMR (CDCl3) δ: 0.38 (1H, m), 0.66 (1H, m), 0.74 (3H, s), 0.93 (3H, s), 1.30-1.40 (2H, m), 1.74 (2H, bs), 2.67 (2H, m), 2.91 (2H, t, J=8 Hz), 4.03 (1H, s), 7.20-7.30 (3H, m), 7.38 (2H, m).
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