C(OC([N:8]1[C@@H:12](/[CH:13]=[C:14](/[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)\[CH3:15])[CH2:11][O:10]C1(C)C)=O)(C)(C)C>CCO.C(Cl)(Cl)Cl.[Pd]>[NH2:8][C@@H:12]([CH2:13][CH:14]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[CH3:15])[CH2:11][OH:10]A solution of (S)-2,2-dimethyl-4-((E)-2-phenyl-propenyl)-oxazolidine-3-carboxylic acid tert-butyl ester (700 mg) in EtOH (30 ml) and CHCl3 (15 ml) was treated with 10% Pd/C (200 mg) and hydrogenated with a balloon overnight. The catalyst was filtered off, washed with EtOH and concentrated. The residue was dissolved in EtOH (10 ml) and treated with 2N HCl (15 ml). The mixture was heated for 90 min to 100° C., then concentrated. The residue was taken up in 1N NaOH and extracted with CH2Cl2/MeOH 4:1. The organic layer was dried over MgSO4, filtrated and concentrated. The crude product was purified by column chromatography (SiO2; gradient: CH2Cl2->CH2Cl2/MeOH 9:1) to give (S)-2-amino-4-phenyl-pentan-1-ol (342 mg) as off-white waxy solid.
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