1: (2R)-2-amino-2-phenyl-1-ethanol With sodium hydride in tetrahydrofuran; mineral oil T=20°C; Inert atmosphere; 2: methyl iodide in tetrahydrofuran; mineral oil T=20°C; 4 h; Inert atmosphereReflux;

1: With sodium hydride in tetrahydrofuran T=20 - 40°C; 2.25 h; 2: With hydrogenchloride in tetrahydrofuran; diethyl ether T=20°C; 3 h;

2-mercapto benzoic acid; 1,4-di(diphenylphosphino)-butane; bis(dibenzylideneacetone)-palladium(0) in tetrahydrofuran T=60°C; 12 h;

1.1: NaH / tetrahydrofuran / 0.17 h / 0 °C 1.2: 68 percent / tetrahydrofuran / 0 - 25 °C 2.1: Pd(dba)2; DPPB; 2-mercaptobenzoic acid / tetrahydrofuran / 12 h / 60 °C View Scheme

1.1: 85 percent / NaHCO3; Bu4NI / tetrahydrofuran; dimethylsulfoxide / 3 h / 60 °C 2.1: NaH / tetrahydrofuran / 0.17 h / 0 °C 2.2: 68 percent / tetrahydrofuran / 0 - 25 °C 3.1: Pd(dba)2; DPPB; 2-mercaptobenzoic acid / tetrahydrofuran / 12 h / 60 °C View Scheme

potassium hydride 1.) THF, overnight, 2.) THF, 3 h; Yield given. Multistep reaction;

1.1: LiAlH4 / tetrahydrofuran / Heating 2.1: MgSO4 / CH2Cl2 / 2 h / 20 °C 3.1: NaH / tetrahydrofuran / 2.25 h / 20 - 40 °C 3.2: 85 percent / 3N HCl / tetrahydrofuran; diethyl ether / 3 h / 20 °C View Scheme