The mixture was stirred overnight (14 h) at room temperature

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The mixture was stirred overnight (14 h) at room temperature. of 2,6-disulfanyl-9-selenabicyclo[3.3.1]nonanes has been described in the literature. and (3). Thiourea (1.52 g, 2 mmol) was added to a solution of compound 2 (3 g, 0.865 mmol) in acetonitrile (120 mL). The mixture was stirred at room temperature for 2 h and then heated under reflux with stirring for 5 h. The formation of white precipitate was observed. Precipitated product was filtered, washed with cold hexane and dried in vacuum, giving bis-isothiouronium salt 3 (4.10 g, 95% yield) as a white powder; mp 219C220 C. 1H-NMR (400 MHz, (5). A solution of methyl iodide (0.26 g, 1.8 mmol) in ethanol (1 mL) was added to a solution of bis-isothiouronium salt 3 (0.35 g, 0.7 mmol) in ethanol (4 mL). Then a solution of sodium hydroxide (80%, 0.2 g, 4 mmol) in ethanol (3 mL) was added dropwise YM348 to the reaction mixture. The mixture was stirred for 8 h at room temperature. Methylene chloride (15 mL) and cold water (15 mL) were added to the reaction mixture. The mixture was transferred to a separatory funnel and the organic layer was separated. The mixture was additionally extracted with methylene chloride (2 10 mL), the organic phase was dried over CaCl2 and the solvent was removed by a rotary evaporator. The residue was dried in vacuum, giving product 5 (0.195 g, 99% yield) as a white powder; mp 64C65 C. 1H NMR (400 MHz, CDCl3): 1.73C1.84 (m, 2H, CH2CHS), 1.93C2.02 (m, 2H, CH2CHSe), 2.03 (s, 6H, CH3), 2.12C2.22 (m, 2H, CH2CHS), 2.64C2.73 (m, 2H, CH2CHSe), 2.97C3.02 (m, 2H, CHS), 3.47C3.54 (m, 2H, CHSe). 13C NMR (100 MHz, CDCl3): 14.25 (CH3), 28.8 (CH2CHSe), 29.2 (CHSe, 1(6). A solution of ethyl bromide (0.28 g, 2.6 mmol) in methanol (1 mL) was added to a solution of bis-isothiouronium salt 3 (0.43 g, 0.86 mmol) in methanol (5 mL). Then, a solution of sodium hydroxide (80%, 0.25 g, 5 mmol) in methanol (4 mL) was added dropwise to the reaction mixture. The mixture was stirred overnight (14 h) at room temperature. Methylene chloride (20 mL) and cold water (20 mL) were added to the reaction mixture. The mixture was transferred to a separatory funnel and the organic layer was separated. The mixture was additionally extracted with methylene chloride (2 10 mL), the organic phase was Rabbit Polyclonal to RPS12 dried over CaCl2 and the solvent was removed by a rotary evaporator. The residue was dried in vacuum, giving product 6 (0.26 g, 98% yield) as a YM348 white powder; mp 59C60 C. 1H NMR (400 MHz, CDCl3): 1.15 (t, 6H, CH3, 3(7) was obtained as a colourless viscous oil (0.276 g, 95% yield) from bis-isothiouronium salt 3 (0.43 g, YM348 0.86 mmol), propyl bromide (0.32 g, 2.6 mmol) and sodium hydroxide (80%, 0.25 g, 5 mmol) in methanol under the same conditions as compound 6. 1H NMR (400 MHz, CDCl3): 0.89 (t, 6H, CH3, 3(8) was obtained as a colourless viscous oil (0.299 g, 95% yield) from bis-isothiouronium salt 3 (0.43 g, 0.86 mmol), butyl bromide (0.35 g, 2.6 mmol) and sodium hydroxide (80%, 0.25 g, 5 mmol) in methanol under the same conditions as compound 6. 1H NMR (400 MHz, CDCl3): 0.82 (t, 6H, CH3, 3(9) was obtained as a colourless viscous oil (0.296 g, 94% yield) from YM348 bis-isothiouronium salt 3 (0.43 g, 0.86 mmol), isobutyl bromide (0.35 g, 2.6 mmol) and sodium hydroxide (80%, 0.25 g, 5 mmol) in methanol under the same conditions as compound 6. 1H NMR (400 MHz, CDCl3): 0.98 (d, 12H, CH3, 3(10). A solution of isopropyl bromide (0.32 g, 2.6 mmol) in methanol (1 mL) was added to a solution of compound 3 (0.43 g, 0.86 mmol) in methanol (5 mL). Then a solution of sodium hydroxide (80%, 0.25 g, 5 mmol) in methanol (4 mL) was added dropwise and the mixture was refluxed for 3 h. Methylene chloride (20 mL) and cold water (20 mL) were added to the reaction mixture. The YM348 mixture was transferred to a separatory funnel and the organic layer was separated. The mixture was additionally extracted with methylene chloride (2 10 mL), the organic phase was dried over CaCl2 and the solvent was removed by a rotary evaporator. The residue was subjected to column chromatography on silica gel (eluent: hexane, then hexane/chloroform 1:10). Compound 10 (0.262 g, 90% yield) was isolated as.