hydrogen; palladium on activated charcoal in ethyl acetate T=20°C; P=760 Torr; 6 h;

hydrogen; palladium on activated charcoal in ethyl acetate T=20°C; P=760 Torr; 22 h;

hydrogen; W-2 Raney Ni in ethanol 36 h; Heating;

hydrogen; platinum(IV) oxide in diethyl ether P=735.5 Torr; 7 h; Ambient temperature;

2,4,6-trimethyl-pyridine; ethylene glycol; dimethyl sulfoxide; [ReV(O)Cl3(PPh3)2] in toluene 3 h; Heating;

sodium in ethanol 5 h; Reflux;

1: With [PtCl2(H2C=CH2)]2 in 1,4-dioxane T=23°C; 0.5 h; 2: With camphor-10-sulfonic acid; acetonitrile in 1,4-dioxane T=20°C; 4 h; 3: With magnesium sulfate in 1,4-dioxane T=20°C; 5 h; Title compound not separated from byproducts;

1: 96 percent / 4-(dimethylamino)pyridine / pyridine / 8 h / Ambient temperature 2: 1.)POCl3 / 1.) CH2Cl2, 0 deg C, 0.5 h, 2.) CH2Cl2, RT, 3 h 3: 86 percent / NaBH4, 5percent aq. NaOH / methanol / 6 h / Ambient temperature 4: 1.) 3-chloroperbenzoic acid, 2.) 10-camphorsulfonic acid / 1.) benzene, RT, 2 h, 2.) benzene, RT, 15 min 5: 97 percent / H2, Na2HPOP4 / 5percent Pd/C / methanol / 2 h 6: 85 percent / zinc triflate / CH2Cl2 / 16 h / Heating 7: 78 percent / H2 / W-2 Raney Ni / ethanol / 36 h / Heating View Scheme

1: 85 percent / zinc triflate / CH2Cl2 / 16 h / Heating 2: 78 percent / H2 / W-2 Raney Ni / ethanol / 36 h / Heating View Scheme

1: 1.)POCl3 / 1.) CH2Cl2, 0 deg C, 0.5 h, 2.) CH2Cl2, RT, 3 h 2: 86 percent / NaBH4, 5percent aq. NaOH / methanol / 6 h / Ambient temperature 3: 1.) 3-chloroperbenzoic acid, 2.) 10-camphorsulfonic acid / 1.) benzene, RT, 2 h, 2.) benzene, RT, 15 min 4: 97 percent / H2, Na2HPOP4 / 5percent Pd/C / methanol / 2 h 5: 85 percent / zinc triflate / CH2Cl2 / 16 h / Heating 6: 78 percent / H2 / W-2 Raney Ni / ethanol / 36 h / Heating View Scheme