1: 86 percent / pyridinium chlorochromate, sodium acetate / CH2Cl2 / 0.75 h / 25 °C 2: 1.) sodium hydride / 1.) ether, 25 deg C, 45 min, 2.) 3 h 3: 98 percent / hydrogen / 5percent Pd-C / methanol / 12 h / 25 °C 4: 86 percent / hydrochloric acid / diethyl ether / 1 h / 25 °C View Scheme

1: 1.) sodium hydride / 1.) ether, 25 deg C, 45 min, 2.) 3 h 2: 98 percent / hydrogen / 5percent Pd-C / methanol / 12 h / 25 °C 3: 86 percent / hydrochloric acid / diethyl ether / 1 h / 25 °C View Scheme

1: 1.) p-CH3C6H4SO3H, 2.) LAH / 1.) C6H6 2: 86 percent / pyridinium chlorochromate, sodium acetate / CH2Cl2 / 0.75 h / 25 °C 3: 1.) sodium hydride / 1.) ether, 25 deg C, 45 min, 2.) 3 h 4: 98 percent / hydrogen / 5percent Pd-C / methanol / 12 h / 25 °C 5: 86 percent / hydrochloric acid / diethyl ether / 1 h / 25 °C View Scheme

1: 1.) sodium hydride / 1.) ether, 25 deg C, 45 min, 2.) 3 h 2: 98 percent / hydrogen / 5percent Pd-C / methanol / 12 h / 25 °C 3: 86 percent / hydrochloric acid / diethyl ether / 1 h / 25 °C View Scheme

1: 98 percent / hydrogen / 5percent Pd-C / methanol / 12 h / 25 °C 2: 86 percent / hydrochloric acid / diethyl ether / 1 h / 25 °C View Scheme

1: Irradiation 2: H2 / Pd 3: (i) , (ii) (oxidation) View Scheme

1: H2 / Pd 2: (i) , (ii) (oxidation) View Scheme

1: H2 / Pd 2: (i) , (ii) (oxidation) View Scheme

(i) , (ii) (oxidation); Multistep reaction;

(i) EtONO, (ii) HCHO; Multistep reaction;