benzyl thiomorpholine-4-carboxylate

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of thiomorpholine (2 g) in 1N NaOH (11.6 mL) was added benzyl chloridocarbonate (1.66 mL) under ice water cooling and the mixture was stirred at ambient temperature for 2 hours. The solution was neutrolized with 1N HCl and extracted with EtOAc twice. The combined organic layer was washed with water and brine, dried over MgSO4 and evaporated in vacuo. The residue was purified by silica gel column chromatography to give benzyl 4-thiomorpholinecarboxylate as a colorless solid (4.8 g). extracted with EtOAc twice The combined organic layer was washed with water and brine dried over MgSO4 evaporated in vacuo The residue was purified by silica gel column chromatography

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of benzyl 4-thiomorpholinecarboxylate (4.8 g) in methanol (30 mL) and H2O (20 mL) was added oxone (16.2 g) under ice water cooling and the mixture was stirred at ambient temperature for 2 hours. The solution was evaporated in vacuo and partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc. The combined organic layer was washed with water and brine, dried over MgSO4 and evaporated in vacuo. The residue was purified by silica gel column chromatography eluting with a mixture of hexane and EtOAc to give benzyl 4-thiomorpholinecarboxylate 1,1-dioxide as a colorless solid (3.8 g). The solution was evaporated in vacuo partitioned between EtOAc and water The aqueous layer was extracted with EtOAc The combined organic layer was washed with water and brine dried over MgSO4 evaporated in vacuo The residue was purified by silica gel column chromatography eluting with a mixture of hexane and EtOAc

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of benzyl 4-thiomorpholinecarboxylate (4.8 g) in methanol (30 mL) and H2O (20 mL) was added oxone (16.2 g) under ice water cooling and the mixture was stirred at ambient temperature for 2 hours. The solution was evaporated in vacuo and partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc. The combined organic layer was washed with water and brine, dried over MgSO4 and evaporated in vacuo. The residue was purified by silica gel column chromatography eluting with a mixture of hexane and EtOAc to give benzyl 4-thiomorpholinecarboxylate 1,1-dioxide as a colorless solid (3.8 g). The solution was evaporated in vacuo partitioned between EtOAc and water The aqueous layer was extracted with EtOAc The combined organic layer was washed with water and brine dried over MgSO4 evaporated in vacuo The residue was purified by silica gel column chromatography eluting with a mixture of hexane and EtOAc

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of thiomorpholine (2 g) in 1N NaOH (11.6 mL) was added benzyl chloridocarbonate (1.66 mL) under ice water cooling and the mixture was stirred at ambient temperature for 2 hours. The solution was neutralized with 1N HCl and extracted with EtOAc twice. The combined organic layer was washed with water and brine, dried over MgSO4 and evaporated in vacuo. The residue was purified by silica gel column chromatography to give benzyl 4-thiomorpholinecarboxylate as a colorless solid (4.8 g). extracted with EtOAc twice The combined organic layer was washed with water and brine dried over MgSO4 evaporated in vacuo The residue was purified by silica gel column chromatography

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of benzyl 4-thiomorpholinecarboxylate (4.8 g) in methanol (30 mL) and H2O (20 mL) was added oxone (16.2 g) under ice water cooling and the mixture was stirred at ambient temperature for 2 hours. The solution was evaporated in vacuo and partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc. The combined organic layer was washed with water and brine, dried over MgSO4 and evaporated in vacuo. The residue was purified by silica gel column chromatography eluting with a mixture of hexane and EtOAc to give benzyl 4-thiomorpholinecarboxylate 1,1-dioxide as a colorless solid (3.8 g). The solution was evaporated in vacuo partitioned between EtOAc and water The aqueous layer was extracted with EtOAc The combined organic layer was washed with water and brine dried over MgSO4 evaporated in vacuo The residue was purified by silica gel column chromatography eluting with a mixture of hexane and EtOAc

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of benzyl 4-thiomorpholinecarboxylate (4.8 g) in methanol (30 mL) and H2O (20 mL) was added oxone (16.2 g) under ice water cooling and the mixture was stirred at ambient temperature for 2 hours. The solution was evaporated in vacuo and partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc. The combined organic layer was washed with water and brine, dried over MgSO4 and evaporated in vacuo. The residue was purified by silica gel column chromatography eluting with a mixture of hexane and EtOAc to give benzyl 4-thiomorpholinecarboxylate 1,1-dioxide as a colorless solid (3.8 g). The solution was evaporated in vacuo partitioned between EtOAc and water The aqueous layer was extracted with EtOAc The combined organic layer was washed with water and brine dried over MgSO4 evaporated in vacuo The residue was purified by silica gel column chromatography eluting with a mixture of hexane and EtOAc

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of thiomorpholine (5 g, 1 mol. equiv.) and triethylamine (5.4 g, 1.1 mol. equiv.) in dichloromethane (200 ml) at 0° C. under nitrogen was slowly added benzyl chloroformate (8.68 g, 1.05 mol. equiv.) over fifteen minutes. The reaction was then allowed to warm to room temperature and stirred for a further sixteen hours. The reaction was washed with a saturated aqueous sodium bicarbonate solution. The organic layer was dried using magnesium sulphate, filtered and the solvent removed under reduced pressure. The residue was purified by flash column chromatography on silica gel eluting with dichloromethane to give the title compound (10 g). TLC=Rf 0.3 (silica, dichloromethane). Found: C, 59.24; H, 6.49; N, 5.78. C12H15NO2S requires C, 59.12; H, 6.23: N, 5.70%. at 0° C. over fifteen minutes The reaction was washed with a saturated aqueous sodium bicarbonate solution The organic layer was dried filtered the solvent removed under reduced pressure The residue was purified by flash column chromatography on silica gel eluting with dichloromethane

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of thiomorpholine (2 g) in 1N NaOH (11.6 mL) was added benzyl chloridocarbonate (1.66 mL) under ice water cooling and the mixture was stirred at ambient temperature for 2 hours. The solution was neutrolized with 1N HCl and extracted with EtOAc twice. The combined organic layer was washed with water and brine, dried over MgSO4 and evaporated in vacuo. The residue was purified by silica gel column chromatography to give benzyl 4-thiomorpholinecarboxylate as a colorless solid (4.8 g). extracted with EtOAc twice The combined organic layer was washed with water and brine dried over MgSO4 evaporated in vacuo The residue was purified by silica gel column chromatography

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of benzyl 4-thiomorpholinecarboxylate (4.8 g) in methanol (30 mL) and H2O (20 mL) was added oxone (16.2 g) under ice water cooling and the mixture was stirred at ambient temperature for 2 hours. The solution was evaporated in vacuo and partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc. The combined organic layer was washed with water and brine, dried over MgSO4 and evaporated in vacuo. The residue was purified by silica gel column chromatography eluting with a mixture of hexane and EtOAc to give benzyl 4-thiomorpholinecarboxylate 1,1-dioxide as a colorless solid (3.8 g). The solution was evaporated in vacuo partitioned between EtOAc and water The aqueous layer was extracted with EtOAc The combined organic layer was washed with water and brine dried over MgSO4 evaporated in vacuo The residue was purified by silica gel column chromatography eluting with a mixture of hexane and EtOAc