[CH3:1][CH:2]([CH3:12])[CH:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:4][NH2:5].[CH:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>C(O)(=O)C.C(Cl)Cl>[CH2:13]([NH:5][CH2:4][CH:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH:2]([CH3:12])[CH3:1])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1A mixture of 3-methyl-2-phenyl-butylamine (1.3 g, 8 mmol), benzaldehyde (271 μL, 2.66 mmol) and CH2Cl2 (50 mL) is stirred for 20 min at RT. NaBH(OAc)3 (840 mg, 3.96 mmol) and acetic acid (154 μL, 2.69 mmol) are added. After 2 h the same amounts as indicated above of benzaldehyde, NaBH(OAc)3 and acetic acid are added once again. This procedure is repeated after 4 h. After stirring for 16 h at RT, saturated NaHCO3 solution is added, the CH2Cl2 layer is removed and the aqueous phase is extracted twice with fresh CH2Cl2. The combined organic layers are dried (Na2SO4), evaporated in vacuo and the residue is purified by flash chromatography (hexane/ethyl acetate). The combined pure fractions are evaporated to afford the title compound as a colourless oil. MS: 254.3 [M+H]+; tR (HPLC, Nucleosil C18; 5-100% CH3CN+0.1% TFA/H2O+0.1% TFA for 8 min, flow 1.5 ml/min): 5.03 min.
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