[CH3:1][N:2]([CH2:10][CH2:11][O:12][CH3:13])[C:3]1([C:8]#[N:9])[CH2:7][CH2:6][CH2:5][CH2:4]1.[C:14]1([Li])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(OCCCC)CCC.[BH4-].[Na+].NC(C1C=CC=CC=1)C1(N(C)C)CCCC1>C1COCC1.CO>[NH2:9][CH:8]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:3]1([N:2]([CH3:1])[CH2:10][CH2:11][O:12][CH3:13])[CH2:7][CH2:6][CH2:5][CH2:4]1The title compound (1.22 g; 42%) was prepared from 1-{methyl[2-(methyloxy)ethyl]amino}cyclopentanecarbonitrile D35 (2.0 g; 11 mmol), and phenyllithium in di-n-butylether (6.7 ml of 1.8M solution; 12 mmol) in THF (25 ml), followed by reaction with sodium borohydride (1.25 g; 33 mmol) in methanol (25 ml) in a similar manner to that described in D2. Mass Spectrum (Electrospray LC/MS). Found 263 (MH+). C16H26N2O requires 262. Ret. time 1.57 min.
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