hydrazine hydrate 8 h; Heating;

1: LiAlH4 / tetrahydrofuran / 23 °C 2: pyridine / 23 °C View Scheme

1: LiAlH4 2: pyridine View Scheme

1: LiAlH4 2: pyridine 3: DMSO View Scheme

1: 88 percent / LiAlH4 / tetrahydrofuran 2: 47 percent / p-CH3-C6H4SO2Cl / pyridine View Scheme

sodium ethanolate

ethanol; platinum Hydrogenation;

1: LiAlH4 / tetrahydrofuran / 23 °C 2: pyridine / 23 °C View Scheme

1: 50 percent / 50percent NaOH, (benzyl)(triethyl)ammonium chloride / 4 h / 40 - 50 °C 2: 83 percent / LiAlH4 / diethyl ether / 2 h 3: 80 percent / triethylamine / CH2Cl2 4: 50 percent / potassium t-butoxide / tetrahydrofuran / 1.5 h View Scheme

1: 84 percent / 50percent NaOH, Et3PhCH2NCl / 6 h / 40 - 50 °C 2: 66 percent / LiAlH4 / diethyl ether / 8 h / Ambient temperature 3: 18 percent / SOCl2 / pyridine / 1.) 0 deg C, 30 min; 2.) reflux, 20 min 4: 45 percent / KO-t-Bu / tetrahydrofuran / 1.5 h 5: 60 percent / CH2Cl2 / 2.5 h / Heating 6: 60 percent / pyridinium hydrobromide perbromide / tetrahydrofuran / 1 h View Scheme