hydrogen; palladium on activated charcoal in cyclohexane T=50°C; P=12001 Torr; 15 h;

1: 73 percent / 1.) Mg, 1,2-dibromoethane / tetrahydrofuran / 1.) reflux, 3.5 h; 2.) reflux, 5 h 2: 1.) p-TsOH*H2O; 2.) hydrogen / 2.) 10percent Pd-C / 1.) benzene, reflux, 2 h; 2.) cyclohexane, 40 deg C, 15 bar, 18 h 3: 74 percent / PCC / CH2Cl2 / 16 h / Ambient temperature 4: 94 percent / BuLi / tetrahydrofuran; hexane / 5 h / Ambient temperature 5: 93 percent / hydrogen / 10percent Pd-C / cyclohexane / 20 h / 40 °C / 7500.6 - 11250.9 Torr 6: 1.) p-TsOH; 2.) hydrogen / 2.) 10percent Pd-C / 1.) benzene, reflux, 5 h; 2.) cyclohexane, 40 deg C, 13 bar, 20 h View Scheme

1: 1.) p-TsOH*H2O; 2.) hydrogen / 2.) 10percent Pd-C / 1.) benzene, reflux, 2 h; 2.) cyclohexane, 40 deg C, 15 bar, 18 h 2: 74 percent / PCC / CH2Cl2 / 16 h / Ambient temperature 3: 94 percent / BuLi / tetrahydrofuran; hexane / 5 h / Ambient temperature 4: 93 percent / hydrogen / 10percent Pd-C / cyclohexane / 20 h / 40 °C / 7500.6 - 11250.9 Torr 5: 1.) p-TsOH; 2.) hydrogen / 2.) 10percent Pd-C / 1.) benzene, reflux, 5 h; 2.) cyclohexane, 40 deg C, 13 bar, 20 h View Scheme

1: 73 percent / 1.) Mg, 1,2-dibromoethane / tetrahydrofuran / 1.) reflux, 3.5 h; 2.) reflux, 5 h 2: 1.) p-TsOH*H2O; 2.) hydrogen / 2.) 10percent Pd-C / 1.) benzene, reflux, 2 h; 2.) cyclohexane, 40 deg C, 15 bar, 18 h 3: 74 percent / PCC / CH2Cl2 / 16 h / Ambient temperature 4: 94 percent / BuLi / tetrahydrofuran; hexane / 5 h / Ambient temperature 5: 93 percent / hydrogen / 10percent Pd-C / cyclohexane / 20 h / 40 °C / 7500.6 - 11250.9 Torr 6: 1.) p-TsOH; 2.) hydrogen / 2.) 10percent Pd-C / 1.) benzene, reflux, 5 h; 2.) cyclohexane, 40 deg C, 13 bar, 20 h View Scheme

1: 1) Mg, 2) CuCl2, LiCl / 1) BrCH2CH2Br, THF, a) sonication, 50 deg C, 30 min, b) reflux, 2 h, 2) THF, a) ice/salt bath, 5 h, b) r.t., overnight 2: 37 percent / Li/Na / hexane; tetrahydrofuran / 1.5 h / 50 °C / sonication 3: 87 percent / H2 / 10percent Pd/C / cyclohexane / 15 h / 50 °C / 12001 Torr 4: 81 percent / TsOH*H2O / benzene / 2 h / Heating 5: 95 percent / H2 / 10percent Pd/C / cyclohexane / 15 h / 50 °C / 12001 Torr View Scheme

1: 1) NaH / 1) THF, -10 to -5 deg C, 2 h, 2) THF, a) rt, 2 h, b) reflux, 2 h 2: 1) Mg, 2) CuCl2, LiCl / 1) BrCH2CH2Br, THF, a) sonication, 50 deg C, 30 min, b) reflux, 2 h, 2) THF, a) ice/salt bath, 5 h, b) r.t., overnight 3: 37 percent / Li/Na / hexane; tetrahydrofuran / 1.5 h / 50 °C / sonication 4: 87 percent / H2 / 10percent Pd/C / cyclohexane / 15 h / 50 °C / 12001 Torr 5: 81 percent / TsOH*H2O / benzene / 2 h / Heating 6: 95 percent / H2 / 10percent Pd/C / cyclohexane / 15 h / 50 °C / 12001 Torr View Scheme

1: 93 percent / PCC / CH2Cl2 / 5 h / Ambient temperature 2: 37 percent / Li/Na / hexane; tetrahydrofuran / 1.5 h / 50 °C / sonication 3: 87 percent / H2 / 10percent Pd/C / cyclohexane / 15 h / 50 °C / 12001 Torr 4: 81 percent / TsOH*H2O / benzene / 2 h / Heating 5: 95 percent / H2 / 10percent Pd/C / cyclohexane / 15 h / 50 °C / 12001 Torr View Scheme

1: 37 percent / Li/Na / hexane; tetrahydrofuran / 1.5 h / 50 °C / sonication 2: 87 percent / H2 / 10percent Pd/C / cyclohexane / 15 h / 50 °C / 12001 Torr 3: 81 percent / TsOH*H2O / benzene / 2 h / Heating 4: 95 percent / H2 / 10percent Pd/C / cyclohexane / 15 h / 50 °C / 12001 Torr View Scheme

1: 94 percent / BuLi / tetrahydrofuran; hexane / 5 h / Ambient temperature 2: 93 percent / hydrogen / 10percent Pd-C / cyclohexane / 20 h / 40 °C / 7500.6 - 11250.9 Torr 3: 1.) p-TsOH; 2.) hydrogen / 2.) 10percent Pd-C / 1.) benzene, reflux, 5 h; 2.) cyclohexane, 40 deg C, 13 bar, 20 h View Scheme

1: 87 percent / 1,3-diaminopropane, 20percent KH in oil / 2 h / Ambient temperature 2: 94 percent / BuLi / tetrahydrofuran; hexane / 5 h / Ambient temperature 3: 93 percent / hydrogen / 10percent Pd-C / cyclohexane / 20 h / 40 °C / 7500.6 - 11250.9 Torr 4: 1.) p-TsOH; 2.) hydrogen / 2.) 10percent Pd-C / 1.) benzene, reflux, 5 h; 2.) cyclohexane, 40 deg C, 13 bar, 20 h View Scheme