1: 65 percent / NaCl, H2O / dimethylsulfoxide / 8 h / 160 °C 2: 76 percent / LAH, EtOH / diethyl ether 3: 80 percent / H2, quinoline / Lindlar's catalyst / hexane 4: 58 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 4 h 5: 1.) NAOH / 1.) THF, < 20 deg C, 2a.) r. t., 5h, 2b.) 60 deg C, 4 h 6: 70 percent / LAH, EtOH / diethyl ether 7: 52 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 4 h View Scheme

1: 85 percent / H2, ethylenediamine / P-2 Ni / ethanol 2: 1) 6M NaOH, 2) 2M HCl / 1) EtOH 3: 75 percent / neat (no solvent) / 0.25 h / 170 °C 4: 1) 1-chloro-N,N,2-trimethyl-1-propenylamine, 2) NEt3 / 1) CH2Cl2, 22 deg C, 2) 22 deg C 5: 2) H2O / 1) ether, RT 6: 72 percent / NaOH / ethanol / 30 h / 22 °C View Scheme

1: 65 percent / NaCl, H2O / dimethylsulfoxide / 8 h / 160 °C 2: 76 percent / LAH, EtOH / diethyl ether 3: 80 percent / H2, quinoline / Lindlar's catalyst / hexane View Scheme

1: 65 percent / NaCl, H2O / dimethylsulfoxide / 8 h / 160 °C 2: 76 percent / LAH, EtOH / diethyl ether 3: 80 percent / H2, quinoline / Lindlar's catalyst / hexane 4: 58 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 4 h View Scheme

1: 65 percent / NaCl, H2O / dimethylsulfoxide / 8 h / 160 °C 2: 76 percent / LAH, EtOH / diethyl ether 3: 80 percent / H2, quinoline / Lindlar's catalyst / hexane 4: 58 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 4 h 5: 1.) NAOH / 1.) THF, < 20 deg C, 2a.) r. t., 5h, 2b.) 60 deg C, 4 h 6: 70 percent / LAH, EtOH / diethyl ether View Scheme

1: 65 percent / NaCl, H2O / dimethylsulfoxide / 8 h / 160 °C 2: 76 percent / LAH, EtOH / diethyl ether 3: 80 percent / H2, quinoline / Lindlar's catalyst / hexane 4: 58 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 4 h 5: 1.) NAOH / 1.) THF, < 20 deg C, 2a.) r. t., 5h, 2b.) 60 deg C, 4 h 6: 70 percent / LAH, EtOH / diethyl ether View Scheme