triethylamine in acetonitrile RefluxInert atmosphere;

1.1: sodium hydroxide / methanol / 1 h / 5 °C 2.1: Dess-Martin periodane / dichloromethane / 2.5 h / 10 °C 3.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 60 °C 4.1: silica gel; sodium tetrahydroborate / chloroform; isopropyl alcohol / 2 h / 20 °C 5.1: zinc; acetic acid / ethanol / 1 h 6.1: dichloromethane / 20 h / 20 °C 7.1: Chiralpak IA / |Resolution of racemate 8.1: sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water / 2 h / 0 °C 9.1: sodium tris(acetoxy)borohydride / N,N-dimethyl acetamide / 2 h / -10 °C 10.1: sulfuric acid / water; N,N-dimethyl acetamide / 18.5 h / 20 °C 10.2: pH 10.2 View Scheme

potassium carbonate in N,N-dimethyl-formamide T=140°C; 18 h;

ammonium acetate in ethanol 6 h; Reflux;

chloro-trimethyl-silane in toluene; acetonitrile T=20 - 50°C; 26 h;

1: 5-fluoro-2-fluorobenzaldehyde; N,N-dimethyl-formamide With chloro-trimethyl-silane in toluene; acetonitrile T=50°C; 7 h; 2: 4-Methyl-benzene sulfinic acid in toluene; acetonitrile T=20 - 50°C; 19 h;

potassium carbonate in N,N-dimethyl-formamide T=120°C; 52 h;

1: acetic anhydride; sodium acetate 2: sodium methylate View Scheme