potassium hydrogensulfate in methanol T=20°C; 2 h;

1: 4-(tert-butyldimethylsilyloxymethyl)benzoic acid methyl ester With ammonia; lithium; tert-butyl alcohol in tetrahydrofuran T=-65 - 15°C; Birch Reduction; 1.25 h; Inert atmosphere; 2: methyl iodide With ammonium chloride in tetrahydrofuran T=-65°C; Birch Reduction; 0.5 h; Inert atmosphere;

1: 88 percent / LiAlH4 / diethyl ether; diethyl ether / 1 h / Heating 2: 87 percent 3: 17 percent / 31percent aq. H2SiF6, Et3N / acetonitrile / 1 h / 0 °C View Scheme

1: 71 percent / LiAlH4 / diethyl ether / 2 h / Heating 2: 62 percent / O2; NaOAc*3H2O / (neocuproine)Pd(OAc)2 / H2O; dimethylsulfoxide / 4 h / 80 °C / 22502.3 Torr View Scheme

1: 88 percent / LiAlH4 / diethyl ether; diethyl ether / 1 h / Heating 2: 87 percent 3: 70 percent / 31percent aq. H2SiF6, Et3N / acetonitrile / 1 h / 0 °C View Scheme

1: With lithium aluminium tetrahydride in diethyl ether T=-78°C; 0.5 h; 2: With ammonium chloride in diethyl ether; water; ethyl acetate

1: 4-(tert-butyldimethylsilyloxymethyl)benzoic acid methyl ester With ammonia; lithium; tert-butyl alcohol in tetrahydrofuran T=-65 - 15°C; Birch Reduction; 1.25 h; Inert atmosphere; 2: methyl iodide With ammonium chloride in tetrahydrofuran T=-65°C; Birch Reduction; 0.5 h; Inert atmosphere;