in tetrahydrofuran T=0°C; 24 h; Inert atmosphere;

sodium hydroxide; hydrogen; nickel in ethanol; water P=760 Torr; 3 h; Ambient temperaturepH 10;

mono-BOC protection;

1: 69 percent / Ph3P, DEAD / tetrahydrofuran / Ambient temperature 2: 88 percent / Zn, 1.) M aq. KH2PO4 / tetrahydrofuran / 4 h / Ambient temperature 3: 95 percent / H2 / 10percent Pd/C / methanol / 1 h / Ambient temperature 4: 72 percent / methanol / Ambient temperature 5: 98 percent / H2, NaOH / Raney nickel / ethanol; H2O / 3 h / 760 Torr / Ambient temperature; pH 10 View Scheme

1: 72 percent / methanol / Ambient temperature 2: 98 percent / H2, NaOH / Raney nickel / ethanol; H2O / 3 h / 760 Torr / Ambient temperature; pH 10 View Scheme

1: 95 percent / H2 / 10percent Pd/C / methanol / 1 h / Ambient temperature 2: 72 percent / methanol / Ambient temperature 3: 98 percent / H2, NaOH / Raney nickel / ethanol; H2O / 3 h / 760 Torr / Ambient temperature; pH 10 View Scheme

1: 88 percent / Zn, 1.) M aq. KH2PO4 / tetrahydrofuran / 4 h / Ambient temperature 2: 95 percent / H2 / 10percent Pd/C / methanol / 1 h / Ambient temperature 3: 72 percent / methanol / Ambient temperature 4: 98 percent / H2, NaOH / Raney nickel / ethanol; H2O / 3 h / 760 Torr / Ambient temperature; pH 10 View Scheme

1: dimethylsulfoxide; diethyl ether / 2 h / Ambient temperature 2: aq. NaOH View Scheme

in methanol T=20°C; 120 h; regioselective reaction;

in methanol T=0 - 20°C; 3 h;