1: 97 percent / SnCl2*2H2O, AcOH, conc. aq. HCl / 72 h / Heating 2: 10.0 M borane methyl sulfide / tetrahydrofuran / 0 - 20 °C 3: triphenylphosphine diiodide, imidazole / CH2Cl2 / Ambient temperature View Scheme

1: hydrogenchloride / dichloromethane; water; acetonitrile / 1 h / 20 °C 2: pyridine / dichloromethane / 12 h / 20 °C / Inert atmosphere 3: immobilized Candida antarctica lipase A; water / 1,4-dioxane / 2 h / 30 °C / pH 5 / Citrate buffer; Enzymatic reaction View Scheme

1: hydrogenchloride / dichloromethane; water; acetonitrile / 1 h / 20 °C 2: pyridine / dichloromethane / 12 h / 20 °C / Inert atmosphere 3: immobilized Candida antarctica lipase A; water / diethyl ether / 2 h / 30 °C / Enzymatic reaction View Scheme

lithium aluminium tetrahydride in tetrahydrofuran 2 h; Heating;