[CH3:1][NH:2][C@H:3]([C:11](O)=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>C1COCC1>[CH3:1][NH:2][C@@H:3]([CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:11][OH:12]To a suspension of N-methyl-L-phenylalanine (20 g, 112 mmol) in THF (1200 mL) cooled to −10° C. was added in small portions lithium aluminium hydride (6.35 g, 167 mmol). After ceasing of the initial exothermic reaction, the cooling bath was removed and the reaction mixture was heated at reflux overnight. Subsequently, another portion of lithium aluminium hydride (4.24 g, 112 mmol) was added after cooling to −10° C., followed by refluxing for an additional 3 h. The reaction mixture was cooled to −40° C., and aqueous 2 N sodium hydroxide was added cautiously. After warming up to r.t., the mixture was filtered, the residue was washed with MTB, and the filtrate was evaporated to give the crude target compound (17.7 g, 96% yield) which was used without further purification.
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