lithium aluminium tetrahydride in tetrahydrofuran 1.5 h; Heating;

1: 1.) 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride, pentafluorophenol, 2.) Et3N / 1.) dichloromethane, RT, 3 h, 2.) dichloromethane, RT, 20 h 2: 1.) SOCl2, 2.) aq. NH3 / 1.) methanol, RT, 2 h, 2.) methanol 3: 92 percent / LiAlH4 / tetrahydrofuran / 1.5 h / Heating View Scheme

1: 1.) SOCl2, 2.) aq. NH3 / 1.) methanol, RT, 2 h, 2.) methanol 2: 92 percent / LiAlH4 / tetrahydrofuran / 1.5 h / Heating View Scheme

1: TEA 2: LiAlH4 / tetrahydrofuran View Scheme

hydrogen; palladium hydroxide on carbon in methanol T=20°C;

1: 68 percent / H2, aq. HCl / 10percent Pd/C / tetrahydrofuran / 760 Torr 2: 83 percent / acetonitrile / 0.5 h / Ambient temperature View Scheme