ammonium acetate; hydrogenchloride; potassium hydroxide; sodium chloride; sodium cyanoborohydride in methanol; water

dimethylsulfide borane complex in tetrahydrofuran 3 h; Heating;

1: 84 percent / K2CO3 / acetone / 5 h / Heating 2: BH3*SMe2 / tetrahydrofuran / 3 h / Heating View Scheme

ammonia

1.1: potassium carbonate; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'- binaphthyl / toluene / 16 h / 130 °C / |Inert atmosphere 2.1: tri-ruthenium(0)dodecacarbonyl; 3,3-dimethyl-butan-2-one / 24 h / 140 °C / |Inert atmosphere 3.1: methyl-magnesium chloride / tetrahydrofuran / 0.17 h / 20 °C 3.2: 1 h / 20 °C 4.1: methyl trifluoromethanesulfonate / dichloromethane / 12 h / 0 °C 4.2: 6 h / 50 °C View Scheme