lithium aluminium tetrahydride in tetrahydrofuran; diethyl ether

triethylamine in ethanol T=0 - 20°C; 1 h;

dimethylsulfide borane complex in tetrahydrofuran T=-10 - 67°C;

sodium tris(acetoxy)borohydride in 1,2-dichloro-ethane T=20°C; 15 h; Inert atmosphere;

sodium tetrahydroborate; boron trifluoride diethyl etherate in tetrahydrofuran

1: Candida antarctica lipase type B / acetone / 24 h / 30 °C / pH 7.5 / aq. phosphate buffer 2: dimethylsulfide borane complex / tetrahydrofuran / -10 - 67 °C View Scheme

1.1: hydrogenchloride / water / 70 °C 2.1: sodium acetate / ethanol / 1 h / 20 °C 2.2: 1 h / 20 °C 2.3: 2.5 h / Reflux 3.1: acetic acid; zinc / 20 °C / Cooling with ice 4.1: Candida antarctica lipase type B / acetone / 24 h / 30 °C / pH 7.5 / aq. phosphate buffer 5.1: dimethylsulfide borane complex / tetrahydrofuran / -10 - 67 °C View Scheme

1.1: sodium acetate / ethanol / 1 h / 20 °C 1.2: 1 h / 20 °C 1.3: 2.5 h / Reflux 2.1: acetic acid; zinc / 20 °C / Cooling with ice 3.1: Candida antarctica lipase type B / acetone / 24 h / 30 °C / pH 7.5 / aq. phosphate buffer 4.1: dimethylsulfide borane complex / tetrahydrofuran / -10 - 67 °C View Scheme

1.1: sodium tungstate monohydrate; dihydrogen peroxide / methanol; water / 18 h / -15 - 20 °C 2.1: hydrogenchloride / water / 70 °C 3.1: sodium acetate / ethanol / 1 h / 20 °C 3.2: 1 h / 20 °C 3.3: 2.5 h / Reflux 4.1: acetic acid; zinc / 20 °C / Cooling with ice 5.1: Candida antarctica lipase type B / acetone / 24 h / 30 °C / pH 7.5 / aq. phosphate buffer 6.1: dimethylsulfide borane complex / tetrahydrofuran / -10 - 67 °C View Scheme

hydrogen; palladium on activated charcoal in methanol 24 h;