in tetrahydrofuran; water T=0 - 30°C;

1: (S)-3,4-dihydro-4-hydroxy-2(3-methoxypropyl)-4H-thieno[3,2-e]-1,2-thiazine-6-sulfonamide-1,1-dioxide With toluene-4-sulfonic acid; triethylamine in tetrahydrofuran T=0 - 20°C; 18 h; 2: ethylamine in tetrahydrofuran T=0 - 20°C; 36 h;

1: With n-butyllithium in tetrahydrofuran; hexane T=-60°C; 8.75 h; Inert atmosphere; 2: With sulfur dioxide in tetrahydrofuran; hexane T=-65 - 20°C; 3: With NaOAc·3H2O; hydroxylamine-o-sulphonic acid in ethyl acetate T=0 - 20°C;

triethylamine in water T=25 - 30°C; pH=7 - 8.5; 2 h;

triethylamine in water T=25 - 30°C; pH=7 - 8.5; 2 h;

1: (R)-3,4-Dihydro-4-hydroxy-2-(3-methoxypropyl)-2H-thieno[3,2-e]-1,2-thiazine-6-sulfonamide 1,1-dioxide With zinc p-toluenesulfonate; triphenylphosphine; diethylazodicarboxylate in tetrahydrofuran T=20 - 80°C; 8 h; 2: ethylamine in tetrahydrofuran T=0 - 20°C; 36 h; Product distribution / selectivity;

1.1: triethylamine / tetrahydrofuran / 0 - 20 °C 2.1: water; tetrahydrofuran / 0 - 20 °C 2.2: pH 1 - 3 3.1: sodium hydrogencarbonate 3.2: 1 h / -40 °C View Scheme

1.1: thiourea / ethanol; water / 2 h / |Reflux; |Large scale 1.2: 3 h / |Reflux; |Large scale 2.1: chlorine / toluene / 0.42 h / 8 °C / |Cooling with ice 3.1: ammonia / 1 h / 5 - 15 °C 4.1: Na2WO4·2H2O; dihydrogen peroxide / water / 19 h / 15 - 35 °C 5.1: pyridinium tribromide; sulfuric acid / ethyl acetate / 1.5 h / 1 - 5 °C / |Large scale 6.1: bis[(1S,2R,3S,5S)-pinan-3-yl]chloroborane / tert-butyl methyl ether / 3.5 h / -40 - -32 °C / |Inert atmosphere 6.2: 2 h / 0 - 22 °C 7.1: potassium carbonate / dimethyl sulfoxide 8.1: n-butyllithium / hexane; tetrahydrofuran / 3.5 h / -70 - -66 °C / |Inert atmosphere 8.2: 20 °C / pH 4 8.3: 15 h / 0 - 25 °C 9.1: acetonitrile / 19 h / 30 - 85 °C / |Reflux 10.1: triethylamine / tetrahydrofuran / 2 h / -10 - -2 °C / |Inert atmosphere 11.1: water / 15 h / 11 - 20 °C View Scheme

1.1: chlorine / toluene / 0.42 h / 8 °C / |Cooling with ice 2.1: ammonia / 1 h / 5 - 15 °C 3.1: Na2WO4·2H2O; dihydrogen peroxide / water / 19 h / 15 - 35 °C 4.1: pyridinium tribromide; sulfuric acid / ethyl acetate / 1.5 h / 1 - 5 °C / |Large scale 5.1: bis[(1S,2R,3S,5S)-pinan-3-yl]chloroborane / tert-butyl methyl ether / 3.5 h / -40 - -32 °C / |Inert atmosphere 5.2: 2 h / 0 - 22 °C 6.1: potassium carbonate / dimethyl sulfoxide 7.1: n-butyllithium / hexane; tetrahydrofuran / 3.5 h / -70 - -66 °C / |Inert atmosphere 7.2: 20 °C / pH 4 7.3: 15 h / 0 - 25 °C 8.1: acetonitrile / 19 h / 30 - 85 °C / |Reflux 9.1: triethylamine / tetrahydrofuran / 2 h / -10 - -2 °C / |Inert atmosphere 10.1: water / 15 h / 11 - 20 °C View Scheme

1: acetonitrile / 19 h / 30 - 85 °C / |Reflux 2: triethylamine / tetrahydrofuran / 2 h / -10 - -2 °C / |Inert atmosphere 3: water / 15 h / 11 - 20 °C View Scheme