oxathiane 2,2-dioxide

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:160.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of Compound 24 (2.55 g, 10.0 mmol) from step (a) of Example 27 and 1-4-butane sultone (2.98 g, 21.9 mmol) was heated in a pressure tube at 160° C. for 17 hours. The mixture was allowed to cool to room temperature, and the resulting mass was triturated with ethyl acetate (40 ml) until a pink solid separated. The solid was collected by centrifugation, washed with ethyl acetate and dried under vacuum to yield 3.58 g (92%) of Compound 26 with the structure: to cool to room temperature the resulting mass was triturated with ethyl acetate (40 ml) until a pink solid separated The solid was collected by centrifugation washed with ethyl acetate dried under vacuum

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 250 mg of 1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)azetidin-2-one (7) were dissolved in 6 ml of absolute dimethylformamide. 337 mg of powdered potassium carbonate and 69 μl of 1,4,-butanesultone were added. The mixture was stirred at room temperature overnight. The reaction solution was filtered and concentrated under oil pump vacuum. The residue was chromatographed on a 10 g SiO2 cartridge (dichloromethane/methanol=5/1) and crystallized from diethyl ether. The product (131 mg) was obtained as a solid. The reaction solution was filtered concentrated under oil pump vacuum The residue was chromatographed on a 10 g SiO2 cartridge (dichloromethane/methanol=5/1) crystallized from diethyl ether

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 160 mg of 3-[3-(4-fluorofluorophenyl)-3-hydroxypropyl]-1-(4-hydroxyphenyl)-4-(4-methoxyphenyl)azetidin-2-one (11) were dissolved in 4 ml of absolute dimethylformamide. 210 mg of powdered potassium carbonate and 42 mg of 1,4,-butanesultone were added. The mixture was stirred at room temperature overnight. The reaction solution was concentrated under oil pump vacuum, taken up in dichloromethane and washed 1× with water. The aqueous phase was acidified with 2N hydrochloric acid and extracted 2× with dichloromethane. The combined organic phases were dried over sodium sulfate and concentrated. The residue was chromatographed on a 10 g SiO2 cartridge (dichloromethane/methanol=5/1). The product (72 mg) was obtained as an oil. The reaction solution was concentrated under oil pump vacuum washed 1× with water extracted 2× with dichloromethane The combined organic phases were dried over sodium sulfate concentrated The residue was chromatographed on a 10 g SiO2 cartridge (dichloromethane/methanol=5/1)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Morpholine (3.56 g) was dissolved in isopropanol (25 ml) and treated with 1,4-butane sultone (5.58 g) at 10° C. The reaction mixture was allowed to warm to room temperature and stirred for 3 days. The white precipitate that had formed was filtered and dried to give the title compound (1.64 g). Mass spec MH+ (found) 224 MH+ (calc) 224. The white precipitate that had formed was filtered dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 72.3 g (0.46 mol) of 2,6-dimethylquinoline and 188 g (1.4 mol) of butanesultone were heated at 145° C. for 4 hours with stirring. After being cooled to room temperature, 500 ml of acetone was added to the reaction mixture, which was cooled with ice for 30 minutes for crystallization. The crystals formed were filtered out, washed with acetone and dried to obtain 127.3 g of 4-[2,6-dimethyl-1quinolinio]butanesulfonate. The yield of the product was 94%. was cooled with ice for 30 minutes for crystallization The crystals formed were filtered out washed with acetone dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 72.3 g (0.46 mol) of 2,6-dimethylquinoline and 188 g (1.4 mol) of butanesultone were heated at 145° C. for 4 hours with stirring. After being cooled to room temperature, 500 ml of acetone was added to the reaction mixture, which was cooled with ice for 30 minutes for crystallization. The crystals formed were filtered out, washed with acetone and dried to obtain 127.3 g of 4-[2,6-dimethyl-1quinolinio]butanesulfonate. The yield of the product was 94%. was cooled with ice for 30 minutes for crystallization The crystals formed were filtered out washed with acetone dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: After 72.3 g (0.46 mol) of 2,6-dimethylquinoline and 188 g (1.4 mol) of butane sultone were heated at 145° C. with stirring for 4 hours, the mixture was allowed to cool to room temperature, and 500 ml of acetone was added thereto. While cooling, crystallization was conducted for 30 minutes. The resulting crystal was recovered by filtration, washed with acetone and dried to obtain 127.3 g (yield: 94%) of 4-[2,6-dimethyl-1-quinolinio]butane sulfonate. While cooling crystallization was conducted for 30 minutes The resulting crystal was recovered by filtration washed with acetone dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: After 72.3 g (0.46 mol) of 2,6-dimethylquinoline and 188 g (1.4 mol) of butane sultone were heated at 145° C. with stirring for 4 hours, the mixture was allowed to cool to room temperature, and 500 ml of acetone was added thereto. While cooling, crystallization was conducted for 30 minutes. The resulting crystal was recovered by filtration, washed with acetone and dried to obtain 127.3 g (yield: 94%) of 4-[2,6-dimethyl-1-quinolinio]butane sulfonate. While cooling crystallization was conducted for 30 minutes The resulting crystal was recovered by filtration washed with acetone dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of cyclohexylamine (2.0 g, 20.2 mmol) in 1,4-dioxane (13 mL) was added 1,4-butane sultone (2.61 g, 19.2 mmol). The solution was heated to reflux for 2 hours. The reaction was cooled to room temperature. The solid was collected by filtration, washed with acetone (2×20 mL) and dried in vacuo. Yield: 52%. 1H NMR (D2O, 500 MHz) δ ppm 2.95 (m, 3H), 2.81 (m, 2H), 1.92 (m, 2H), 1.67 (m, 6H), 1.52 (m, 1H), 1.18 (m, 4H), 1.02 (m, 1H). 13C (D2O, 125 MHz) δ ppm 57.32, 50.31, 44.01, 29.02, 24.84, 24.68, 24.07, 24.55. ES-MS 236 (M+1). The solution was heated to reflux for 2 hours The solid was collected by filtration washed with acetone (2×20 mL) dried in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-adamantanamine (1.06 g, 7.0 mmol) in 1,4-dioxane (6 mL) was added 1,4-butane sultone (955 mg, 6.7 mmol). The solution was stirred at reflux for 5 hours. The reaction was cooled to room temperature. The solid was collected by filtration. It was suspended in EtOH (25 mL) and the mixture was heated to reflux for 1 minute before the solid was filtered. It was washed with EtOH (1×15 mL) and dried in vacuo. Yield: 55%. 1H NMR (D2O, 500 MHz) δ ppm 3.29 (m, 1H), 2.97 (m, 2H), 2.83 (m, 2H), 2.02 (m, 2H), 1.83 (m, 2H), 1.68 (m, 14H). 13C NMR (D2O, 125 MHz) δ ppm 63.07, 50.25, 45.03, 36.55, 36.31, 29.85, 29.05, 26.68, 26.41, 24.47, 21.61. ES-MS 286 (M−1). at reflux for 5 hours The solid was collected by filtration the mixture was heated to reflux for 1 minute before the solid was filtered It was washed with EtOH (1×15 mL) dried in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of veratrylamine (1.50 g, 9.0 mmol) in 1,4-dioxane (8 mL) was added 1,4-butane sultone (1.21 g, 8.5 mmol) at room temperature. The mixture was then heated at reflux for 2 hours. The reaction was cooled to room temperature. The solid was collected by filtration, washed with acetone (2×25 mL) and dried on pump. Yield: 18%. 1H NMR (D2O, 500 MHz) δ 6.96 (m, 3H), 4.04 (s, 2H), 3.74 (m, 6H), 2.95 (t, 2H, J=6.8 Hz), 2.80 (t, 2H, J=7.3 Hz), 1.68, (m, 4H). 13C (D2O, 125 MHz) δ ppm 149.19, 148.50, 123.82, 123.36, 113.25, 112.17, 55.91, 50.88, 50.24, 46.41, 24.55, 21.50. ES-MS 302 (M−1). The mixture was then heated at reflux for 2 hours The solid was collected by filtration washed with acetone (2×25 mL) dried on pump