1: N,N-dicyclohexylmethylamine; Pd0(tris(tert-butyl)phosphine)2 / 2-methyl tetrahydrofuran / 70 - 86 °C 2: 5 palladium on charcoal; hydrogen; sodium carbonate / 2-methyl tetrahydrofuran; ethanol / 50 °C / 750.08 Torr / |Inert atmosphere 3: 5 palladium on charcoal; hydrogen; sodium carbonate / water; toluene / 50 - 55 °C / 750.08 Torr / |Inert atmosphere 4: Vitride® / toluene / 5 - 25 °C / |Inert atmosphere; |Cooling with ice 5: (S)-α-hydroxybenzeneacetic acid / 2-methyl tetrahydrofuran / 70 °C 6: triethylamine; pyridine / dichloromethane / 10 - 20 °C 7: hydrogenchloride / water; acetonitrile / 1 h / 50 °C / pH 2 - 2.5 View Scheme

N,N-dicyclohexylmethylamine; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine in 1,4-dioxane T=80°C; 18 h; Product distribution / selectivity;