lithium aluminium tetrahydride in tetrahydrofuran T=0°C; Inert atmosphere;

1: With 9-borabicyclo[3.3.1]nonane dimer in tetrahydrofuran T=0°C; 2: With sodium hydroxide; dihydrogen peroxide in tetrahydrofuran; water T=0 - 20°C; Further stages.;

sodium tetrahydroborate in methanol T=-78 - 20°C; 12 h;

triethylamine in dichloromethane T=20°C; 1 h;

lithium aluminium tetrahydride in tetrahydrofuran T=0 - 20°C; Inert atmosphere;

sodium tetrahydroborate in methanol T=-78 - 20°C; Inert atmosphere;

lithium aluminium tetrahydride in tetrahydrofuran 2 h; Heating;

1.1: 90 percent / thionyl chloride; triethylamine / CH2Cl2 / 0.75 h / 0 °C 2.1: 80 percent / sodium azide / dimethylformamide / 48 h / 80 °C 3.1: 88 percent / Et3N; hydrogen / Pd/C / ethyl acetate / 12 h / 20 °C / 760.05 Torr 4.1: sodium hydride / tetrahydrofuran; various solvent(s) / 0.5 h / 0 °C 4.2: 82 percent / tetrahydrofuran; various solvent(s) / 2 h / 0 °C 5.1: 80 percent / tri-n-butyltin hydride; AIBN / toluene / Heating 6.1: 81 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating View Scheme

1.1: 88 percent / Et3N; hydrogen / Pd/C / ethyl acetate / 12 h / 20 °C / 760.05 Torr 2.1: sodium hydride / tetrahydrofuran; various solvent(s) / 0.5 h / 0 °C 2.2: 82 percent / tetrahydrofuran; various solvent(s) / 2 h / 0 °C 3.1: 80 percent / tri-n-butyltin hydride; AIBN / toluene / Heating 4.1: 81 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating View Scheme

1.1: 83 percent / (DHQ)2PHAL; NMO; OsO4 / 2-methyl-propan-2-ol; H2O / 24 h / 20 °C 2.1: 90 percent / thionyl chloride; triethylamine / CH2Cl2 / 0.75 h / 0 °C 3.1: 80 percent / sodium azide / dimethylformamide / 48 h / 80 °C 4.1: 88 percent / Et3N; hydrogen / Pd/C / ethyl acetate / 12 h / 20 °C / 760.05 Torr 5.1: sodium hydride / tetrahydrofuran; various solvent(s) / 0.5 h / 0 °C 5.2: 82 percent / tetrahydrofuran; various solvent(s) / 2 h / 0 °C 6.1: 80 percent / tri-n-butyltin hydride; AIBN / toluene / Heating 7.1: 81 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating View Scheme