C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH2:15]([NH2:23])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[C:24]1([CH2:30][CH:31]=O)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.OP([O-])(O)=O.[K+]>CO>[CH2:15]([NH:23][CH2:31][CH2:30][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1Sodiumtriacetoxyborohydride (8.87 g, 41.3 mmol) is added in small portions at 0° C. to a stirred solution of phenethylamine (5.0 g, 41.3 mmol) and phenylacetaldehyde (4.96 g, 41.3 mmol) in methanol (50 ml). The reaction mixture is stirred at rt overnight, poured onto saturated aqueous KH2PO4 solution and extracted twice with EtOAc. The solvent is evaporated, the residue is taken up in 1N HCl and washed twice with dichloromethane. The aqueous layer is adjusted to pH 9 by the addition of ammonium hydroxide solution and extracted with dichloromethane. Drying the combined organic layers over Na2SO4 and evaporating the solvents give crude title compound as a pale yellow oil.
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