[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9](=O)[C@H:10]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=1)[NH2:11].O.[OH-].[Na+]>O1CCCC1>[NH2:11][C@@H:10]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=1)[CH2:9][OH:8]
To a suspension of lithium aluminum hydride (7.75 g) in tetrahydrofuran (200 ml) is gradually added dropwise a solution of 3-(3,4-dimethoxyphenyl)-L-alanine methyl ester (12.2 g) in tetrahydrofuran (100 ml) at 0° C. The reaction mixture is stirred at 0° C. for 30 minutes, and then thereto are added dropwise water (7.7 ml), 10% aqueous sodium hydroxide solution (7.7 ml) and water (23.1 ml). The reaction mixture is stirred at room temperature overnight, and filtered through a cerite pad. The filtrate is concentrated to give (2S)-2-amino-3-(3,4-dimethoxyphenyl)-1-propanol (10.8 g) as an brown oily product.
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