lithium borohydride; chloro-trimethyl-silane in tetrahydrofuran T=20°C; Reduction; 16 h;

1: With triethylamine in methanol; diethyl ether T=-10°C; 1 h; 2: With sodium tetrahydroborate in methanol T=0 - 20°C;

chiral stationary phase including isopropyl-functionalized CF6 in methanol; acetic acid; triethylamine; acetonitrile T=20°C; Purification / work up;

hydrogen; palladium on activated charcoal

lithium aluminium tetrahydride

T=100°C; 2 h;

1.1: 20 - 80 °C 1.2: 1 h 1.3: DOWEX50wx8 / pH 7 2.1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C 2.2: 48 h 3.1: bis(trichloromethyl) carbonate; 4-methyl-morpholine / dichloromethane / 3.08 h / -78 - -30 °C 4.1: dichloromethane / 72 h / 20 °C 5.1: potassium carbonate; methanol / 0.5 h / 20 °C 5.2: 20 °C View Scheme

sodium hydride in tetrahydrofuran T=20°C; 20 h;

1: pyridine / 2.5 h / 0 °C 2: sodium hydroxide / diethyl ether; H2O / 1.5 h / 0 °C View Scheme