[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:7][C@@H:8]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]([N:11]([CH3:13])[CH3:12])=O.C(OCC)(=O)C.[OH-].[Na+]>CCOCC.O1CCCC1>[CH2:14]([C@H:8]([NH2:7])[CH2:9][N:11]([CH3:13])[CH3:12])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1Lithium aluminum hydride (759 mg) was suspended in anhydrous ether (20 ml) with ice cooling in the nitrogen gas atmosphere and then a solution of (2S)-2-amino-N1,N1-dimethyl-3-phenylpropionamide (1.92 g) in anhydrous tetrahydrofuran (10 ml) was dropwise added to the resulting suspension. This mixture was stirred at room temperature for 1.5 hour. Ethyl acetate was gradually and dropwise added to the reaction liquid till the latter did not undergo foaming any more, with ice cooling. Then a 2N aqueous sodium hydroxide solution was added to the reaction liquid and the resulting mixture was extracted with chloroform. The organic phase thus obtained was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resulting oily product was purified through the silica gel column chromatography to give the title compound (Reference Compound 1-1, 1.35 g).
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