pyridine; hydrogen; palladium on activated charcoal in benzene T=25°C; P=760 Torr; 1 h; Yield given. Yields of byproduct given;

lithium aluminium tetrahydride in diethyl ether T=-45 - 5°C;

1: 1) NaH / 1) THF, 0 deg C, 30 min, 2) THF, 0 deg C, 5 min 2: 24 percent / 30percent H2O2 / CH2Cl2 / 1) 0 deg C, 1 h, 2) 25 deg C, 4 h 3: 95 percent / 425 °C / 0.01 Torr 4: 1) (+)-β-chlorodiisopinocamphenylborane, 2) diethanolamine / 1) THF, -30 deg C, 5 days, 2) Et2O, 2 h 5: 48 percent / mercury(II) acetate / 24 h / 135 - 140 °C 6: H2 / 10percent Pd/C / ethanol / 760 Torr View Scheme

1: 24 percent / 30percent H2O2 / CH2Cl2 / 1) 0 deg C, 1 h, 2) 25 deg C, 4 h 2: 95 percent / 425 °C / 0.01 Torr 3: 1) (+)-β-chlorodiisopinocamphenylborane, 2) diethanolamine / 1) THF, -30 deg C, 5 days, 2) Et2O, 2 h 4: 48 percent / mercury(II) acetate / 24 h / 135 - 140 °C 5: H2 / 10percent Pd/C / ethanol / 760 Torr View Scheme

1: 1) (+)-β-chlorodiisopinocamphenylborane, 2) diethanolamine / 1) THF, -30 deg C, 5 days, 2) Et2O, 2 h 2: 48 percent / mercury(II) acetate / 24 h / 135 - 140 °C 3: H2 / 10percent Pd/C / ethanol / 760 Torr View Scheme

1: 95 percent / 425 °C / 0.01 Torr 2: 1) (+)-β-chlorodiisopinocamphenylborane, 2) diethanolamine / 1) THF, -30 deg C, 5 days, 2) Et2O, 2 h 3: 48 percent / mercury(II) acetate / 24 h / 135 - 140 °C 4: H2 / 10percent Pd/C / ethanol / 760 Torr View Scheme

1: 95 percent / 425 °C / 0.01 Torr 2: 1) (+)-β-chlorodiisopinocamphenylborane, 2) diethanolamine / 1) THF, -30 deg C, 5 days, 2) Et2O, 2 h 3: 48 percent / mercury(II) acetate / 24 h / 135 - 140 °C 4: H2 / 10percent Pd/C / ethanol / 760 Torr View Scheme

1: 48 percent / mercury(II) acetate / 24 h / 135 - 140 °C 2: H2 / 10percent Pd/C / ethanol / 760 Torr View Scheme

water; acetic acid

1: 40 percent / TsOH / benzene / Heating 2: 100 percent / hydrogen, NaOAc / Pd/C / ethyl acetate 3: 85 percent / H2O, HOAc View Scheme