hydrogenchloride; water T=85°C; 12 h; Inert atmosphere;

sodium hydroxide in ethanol T=60°C; 1 h;

hydrogenchloride 1) (R)-oxynitrilase, Avicel cellulose, 0.02 M sodium acetate buffer, diisopropylether, 0 deg C, 41h, 2) a) r.t., 16h, b) reflux, 5h; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

hydrogenchloride; water T=85°C; 12 h; optical yield given as percent ee;

hydrogenchloride; water T=85°C; 16 h; optical yield given as percent ee;

1: 278 g / 40percent H2SO4 / H2O / 0.5 h / 8 - 15 °C 2: 7.4 percent / conc HCl / 240 h / Ambient temperature View Scheme

1.1: water; sulfuric acid; sodium nitrite / 5 - 20 °C / |Inert atmosphere 2.1: toluene-4-sulfonic acid / hexane / |Inert atmosphere; |Dean-Stark; |Reflux 3.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.75 h / -78 °C / |Inert atmosphere 3.2: 4 h / -78 - -30 °C / |Inert atmosphere 4.1: potassium hydroxide / methanol; water / 0.5 h / |Inert atmosphere; |Reflux View Scheme

1.1: toluene-4-sulfonic acid / hexane / |Inert atmosphere; |Dean-Stark; |Reflux 2.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.75 h / -78 °C / |Inert atmosphere 2.2: 4 h / -78 - -30 °C / |Inert atmosphere 3.1: potassium hydroxide / methanol; water / 0.5 h / |Inert atmosphere; |Reflux View Scheme

1.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.75 h / -78 °C / |Inert atmosphere 1.2: 4 h / -78 - -30 °C / |Inert atmosphere 2.1: potassium hydroxide / methanol; water / 0.5 h / |Inert atmosphere; |Reflux View Scheme

1: 38 percent / NaBH4 / ethanol / 1.5 h / Ambient temperature 2: pyridine / CH2Cl2 / Ambient temperature 3: 386 mg / 2N NaOH / ethanol / 0.5 h / 60 °C 4: CrO3 / acetone / 1.) 5 min., 0 deg C, 2.) room temp., 15 min. 5: 89 percent / CF3CO3H, Na2HPO4 / CH2Cl2 / Ambient temperature 6: 39 percent / 2N NaOH / ethanol / 1 h / 60 °C View Scheme