hydrogenchloride in hexane-Et2O; Et2O-dioxane; ethanol; water

1: in 1-methyl-pyrrolidin-2-one 1 h; 2: With phosphazene base P1-t-bu-tris(tetramethylene) in 1-methyl-pyrrolidin-2-one T=20°C; 14 h; 3: With hydrogenchloride in tetrahydrofuran 5 h;

thionyl chloride 4 h; Heating;

1: 88 percent / NaHCO3 / tetrahydrofuran; H2O / 16 h / Ambient temperature 2: 71.4 percent / H2 / 10percent Pd/C / ethanol / 18 h / 3040 Torr 3: 1.) borane*THF complex 2.) HCl / 1.) THF, 60 deg C, 20 h 2.) methanol, reflux, 2 h View Scheme

(i) Et3N, Et2O, (ii) aq. NH3; Multistep reaction;