4-(bromomethyl)-4-methyl-1,3-oxazolidin-2-one

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

実験手順: A solution of 4-(bromomethyl)-4-methyloxazolidin-2-one (1.33 g, 6.86 mmol) in MeOH (10 ml) was cooled to 0° C. and tert-butylhypochlorite (1.0 ml, 8.4 mmol) as added dropwise. The solution was stirred for 30 min, concentrated in vacuo, and the residue purified by flash chromatography (20% to 60% ethyl acetate in hexanes) to afford the title compound as a white solid (960 mg, 4.20 mmol, 61%). 1H NMR (CDCl3, 400 MHz) δ 1.57 (s, 3H), 3.45 (d, J=10.4 Hz, 1H), 3.60 (d, J=10.8 Hz, 1H), 4.20 (d, J=8.8 Hz, 1H), 4.51 (d, J=8.8 Hz, 1H). LRMS (ESI/APCI): 228 [M+H]+. concentrated in vacuo the residue purified by flash chromatography (20% to 60% ethyl acetate in hexanes)

反応条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 4-(chloromethyl)-4-methyloxazolidin-2-one (1.49 g, 9.96 mmol) in DMF (100 ml) was added sodium bromide (11.02 g, 107 mmol), and the suspension heated to 80° C. for 6 h. The suspension was concentrated in vacuo and the residue purified by flash chromatography (30% to 60% ethyl acetate in hexanes) to give the title compound as a white solid (1.33 g, 6.86 mmol, 66%). 1H NMR (CDCl3, 400 MHz) δ 1.54 (s, 3H), 3.47 (s, 2H), 4.14 (d, J=9.2 Hz, 1H), 4.35 (d, J=8.8 Hz, 1H), 6.24 (br s, 1H). LRMS (ESI/APCI): 194 [M+H]+. The suspension was concentrated in vacuo the residue purified by flash chromatography (30% to 60% ethyl acetate in hexanes)

反応条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 4-(chloromethyl)-4-methyloxazolidin-2-one (1.49 g, 9.96 mmol) in DMF (100 ml) was added sodium bromide (11.02 g, 107 mmol), and the suspension heated to 80° C. for 6 h. The suspension was concentrated in vacuo and the residue purified by flash chromatography (30% to 60% ethyl acetate in hexanes) to give the title compound as a white solid (1.33 g, 6.86 mmol, 66%). 1H NMR (CDCl3, 400 MHz) δ 1.54 (s, 3H), 3.47 (s, 2H), 4.14 (d, J=9.2 Hz, 1H), 4.35 (d, J=8.8 Hz, 1H), 6.24 (br s, 1H). LRMS (ESI/APCI): 194 [M+H]+. The suspension was concentrated in vacuo the residue purified by flash chromatography (30% to 60% ethyl acetate in hexanes)

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

実験手順: A solution of 4-(bromomethyl)-4-methyloxazolidin-2-one (1.33 g, 6.86 mmol) in MeOH (10 ml) was cooled to 0° C. and tert-butylhypochlorite (1.0 ml, 8.4 mmol) as added dropwise. The solution was stirred for 30 min, concentrated in vacuo, and the residue purified by flash chromatography (20% to 60% ethyl acetate in hexanes) to afford the title compound as a white solid (960 mg, 4.20 mmol, 61%). 1H NMR (CDCl3, 400 MHz) δ 1.57 (s, 3H), 3.45 (d, J=10.4 Hz, 1H), 3.60 (d, J=10.8 Hz, 1H), 4.20 (d, J=8.8 Hz, 1H), 4.51 (d, J=8.8 Hz, 1H). LRMS (ESI/APCI): 228 [M+H]+. concentrated in vacuo the residue purified by flash chromatography (20% to 60% ethyl acetate in hexanes)

反応条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 4-(chloromethyl)-4-methyloxazolidin-2-one (1.49 g, 9.96 mmol) in DMF (100 ml) was added sodium bromide (11.02 g, 107 mmol), and the suspension heated to 80° C. for 6 h. The suspension was concentrated in vacuo and the residue purified by flash chromatography (30% to 60% ethyl acetate in hexanes) to give the title compound as a white solid (1.33 g, 6.86 mmol, 66%). 1H NMR (CDCl3, 400 MHz) δ 1.54 (s, 3H), 3.47 (s, 2H), 4.14 (d, J=9.2 Hz, 1H), 4.35 (d, J=8.8 Hz, 1H), 6.24 (br s, 1H). LRMS (ESI/APCI): 194 [M+H]+. The suspension was concentrated in vacuo the residue purified by flash chromatography (30% to 60% ethyl acetate in hexanes)