[NH2:1][C@@H:2]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]([N:5]([CH3:7])[CH3:6])=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].C1(C)C=CC=CC=1.CCOCC>O1CCCC1.C(OCC)(=O)C>[CH3:7][N:5]([CH3:6])[CH2:3][C@@H:2]([NH2:1])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1
To a solution of (S)-2-amino-N,N-dimethyl-3-phenyl-propionamide (1.0 g, 5.2 mmol) in tetrahydrofuran (10 mL) was added a solution of lithium aluminum hydride in tetrahydrofuran and toluene (3.5 M, 7.4 mL, 26 mmol) dropwise. The mixture was heated to reflux for 4 h after addition and then cooled. Ether (20 mL) was added. Ethyl acetate was added dropwise until all the lithium aluminum hydride was consumed. Sodium hydroxide (1M, 20 mL) was added and the mixture was stirred for 30 min. The mixture was extracted three times with ether. The combined organic extracts were washed with brine, dried over sodium sulfate and evaporated to give (S)—N1,N1-dimethyl-3-phenyl-propane-1,2-diamine (0.60 g, 65%)
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