1: 98 percent / hydrogen / 5percent Pd/C / acetic acid / 15 h / 20 °C / 15200 Torr 2: 90 percent / TsOH / 16 h / 20 °C 3: 1) DIBAH, 2) water / 1) -10 deg C, toluene, 1.5 h, toluene, THF, 2) 20 deg C, 2 h 4: 97 percent / 10percent HCl / tetrahydrofuran / 16 h / 20 °C View Scheme

1: TsOH / 10 h / Ambient temperature 2: 98 percent / (i-Bu)2AlH / toluene; tetrahydrofuran / -10 °C 3: pyridine / 15 h / -10 °C 4: 75 percent / Li2CuCl4 / diethyl ether; tetrahydrofuran / 2 h / -78 °C 5: aq.HCl / acetone / 4 h / 25 °C 6: (i-Bu)2AlH / diethyl ether; toluene / -10 deg C, 1.5h; 25 deg C,15h 7: pyridine 8: diethyl ether; tetrahydrofuran / 2 h / -78 °C View Scheme

1: 98 percent / hydrogen / 5percent Pd/C / acetic acid / 15 h / 20 °C / 15200 Torr 2: 90 percent / TsOH / 16 h / 20 °C 3: 1) DIBAH, 2) water / 1) -10 deg C, toluene, 1.5 h, toluene, THF, 2) 20 deg C, 2 h 4: 97 percent / 10percent HCl / tetrahydrofuran / 16 h / 20 °C 5: 49 percent / piperidine / 1) pyridine, 20 deg C, 16 h, 2) 110 - 115 deg C, 1 h View Scheme

1: 1) DMSO-C6H6, 20 deg C, 20 min, 2) hydrolysis View Scheme

in diethyl ether 0.0333333 h;

1: 90 percent / p-toluenesulfonic acid / 10 h / Ambient temperature 2: 99 percent / 5percent aq. hydrochloric acid / acetone / 4 h / Ambient temperature View Scheme

1: 85 percent / diethyl ether / 0.03 h 2: 2.) dilute aq. HCl; / 1.) benzene, boiling, 10 h, 2.) 40 deg C, 15 min; 3.) room temperature, 2 h; 3: 90 percent / conc. HCl / 5 h / 90 °C View Scheme

1: 85 percent / diethyl ether / 0.03 h 2: 2.) dilute aq. HCl; / 1.) benzene, boiling, 10 h, 2.) 40 deg C, 15 min; 3.) room temperature, 2 h; 3: conc. HCl / Heating View Scheme

1: 85 percent / diethyl ether / 0.03 h 2: 85 percent / tetrahydrofuran / 0.5 h / 0 °C 3: 85 percent / pyridinium chlorochromate / CH2Cl2 / 1.5 h / Ambient temperature 4: CH3ONa / methanol / 0.33 h / 30 - 35 °C 5: 1.) CH3ONa, 2.) H2SO4; / methanol / -5 °C 6: conc. HCl / propan-2-ol; CHCl3 / 1 h / Ambient temperature 7: 1percent aq. NaOH / ethanol / 0.25 h / 75 - 80 °C 8: conc. H2SO4 / benzene / 12 h / Heating View Scheme

1: TsOH / 10 h / Ambient temperature 2: 98 percent / (i-Bu)2AlH / toluene; tetrahydrofuran / -10 °C 3: pyridine / 15 h / -10 °C View Scheme