potassium carbonate in dichloromethane; water 2 h;

in benzene 6 h; Heating;

1: H2 / PtO2 / ethanol 2: p-toluenesulfonic acid monohydrate / benzene / 44 h / Heating 3: LiAlH4 / diethyl ether / 3 h / Heating View Scheme

1: H2 / PtO2 / ethanol 2: p-toluenesulfonic acid monohydrate / benzene / 44 h / Heating 3: LiAlH4 / diethyl ether / 3 h / Heating 4: 1.) NaH / 1.) DMSO,RT, 2 h, 2.) DMSO, RT, 2 h View Scheme

1: H2 / PtO2 / ethanol 2: p-toluenesulfonic acid monohydrate / benzene / 44 h / Heating 3: LiAlH4 / diethyl ether / 3 h / Heating 4: 1.) NaH / 1.) DMSO,RT, 2 h, 2.) DMSO, RT, 2 h 5: 7.2 g / p-toluenesulfonic acid / acetone / 6.5 h / Heating View Scheme

1: H2 / PtO2 / ethanol 2: p-toluenesulfonic acid monohydrate / benzene / 44 h / Heating 3: LiAlH4 / diethyl ether / 3 h / Heating 4: 1.) NaH / 1.) DMSO,RT, 2 h, 2.) DMSO, RT, 2 h 5: 7.2 g / p-toluenesulfonic acid / acetone / 6.5 h / Heating 6: 1.) Me2NH*HCl 2.) Ac2O / 1.) acetic acid, water, reflux, 17 h, 2.) acetic acid, 100 deg C, 7 h View Scheme