[CH3:1][N:2]([CH3:10])[C:3]([CH2:8][CH3:9])([CH2:6][CH3:7])[C:4]#[N:5].[C:11]1([Li])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[BH4-].[Na+].CC(N1CCCC1)(C)C(N)C1C=CC=CC=1>C(OCCCC)CCC.C1COCC1.CO>[NH2:5][CH:4]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:3]([N:2]([CH3:10])[CH3:1])([CH2:8][CH3:9])[CH2:6][CH3:7]The title compound (11.12 g, 88%) was prepared from 2-(dimethylamino)-2-ethylbutanenitrile D19 (8.05 g, 0.0575 mol) and phenyllithium in dibutylether (64 ml of a 1.8M solution; 0.115 mol) in THF (350 ml), followed by reaction with sodium borohydride (3.9 g, 0.103 mol) in methanol (300 ml) in a similar manner to that described in D5. 1H NMR (CDCl3) δ: 0.72 (3H, t, J=7.6 Hz), 0.97 (3H, t, J=7.6 Hz), 1.40-1.68 (4H, m), 1.70 (2H, br, m), 2.43 (6H, s), 4.09 (1H, s), 7.19-7.43 (5H, m).
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