5-(羟甲基)-4,4-二甲基-1,3-恶唑烷-2-one

反应条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Thionyl chloride (0.13 ml, 1.72 mmol) was added to a mixture of 5-(hydroxymethyl)-4,4-dimethyloxazolidin-2-one (50 mg, 0.34 mmol) in pyridine (1 mL) at −20° C. The mixture was allowed to stir for 15 minutes and then warmed to 60° C. for 1 hour. The mixture was concentrated under reduced pressure and the residue was purified by column chromatography on silica (20-100% ethyl acetate/hexanes) to afford 5-(chloromethyl)-4,4-dimethyloxazolidin-2-one. 1H NMR (500 MHz, CDCl3) δ 6.20 (br s, 1H), 4.38-4.35 (m, 1H), 3.75-3.70 (m, 1H), 3.62-3.57 (m, 1H), 1.42 (s, 3H), 1.31 (s, 3H). The mixture was concentrated under reduced pressure the residue was purified by column chromatography on silica (20-100% ethyl acetate/hexanes)

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a 0° C. solution of 5-(hydroxymethyl)-4,4-dimethyloxazolidin-2-one (250 mg, 1.72 mmol) in 2 mL of methanol was added tertbutyl hypochlorite (290 uL, 2.58 mmol). The reaction was stirred at 0° C. for 1 hour, then concentrated to a crude residue under reduced pressure. The crude product was purified by column chromatography (20 to 80% ethyl acetate in hexanes) to give the title compound as a clear liquid (248 mg, 1.38 mmol, 80%). 1H NMR (CDCl3, 400 MHz) δ 1.29 (s, 3H), 1.42 (s, 3H), 2.28-2.31 (dd, J=4.8, 7.7 1H), 3.85-3.88 (m, 1H), 3.91-3.98 (m, 1H), 4.37-4.40 (dd, J=4.7 6.9 Hz, 1H). LRMS (ESI/APCI) m/z 180 [M+H]+. concentrated to a crude residue under reduced pressure The crude product was purified by column chromatography (20 to 80% ethyl acetate in hexanes)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of 5-((benzyloxy)methyl)-4,4-dimethyloxazolidin-2-one (2.6 g, 11 mmol) in EtOH (40 ml) was added 500 mg of 10% Pd/C (wet, Degussa type E101). The vessel was pressurized with H2 (450 psi) and the suspension stirred for 24 h. An additional 500 mg of 10% Pd/C was added and the reaction was stirred under 450 PSI H2 for 5 days. The mixture was filtered through celite, concentrated in vacuo, and purified by column chromatography (1 to 10% methanol in dichloromethane) to give a clear liquid which solidified to a white solid upon standing (1.8 g, 12 mmol, 100%). 1H NMR (CDCl3, 400 MHz) δ 1.30 (s, 3H), 1.41 (s, 3H), 2.45 (br s, 1H), 3.76-3.81 (m, 1H), 3.87-3.92 (m, 1H), 4.30-4.32 (dd, J=4.4, 7.2 Hz, 1H) 5.59 (br s, H). LRMS (ESI/APCI) m/z 146 [M+H]+. the reaction was stirred under 450 PSI H2 for 5 days The mixture was filtered through celite concentrated in vacuo purified by column chromatography (1 to 10% methanol in dichloromethane) to give a clear liquid which

反应条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Thionyl chloride (0.13 ml, 1.72 mmol) was added to a mixture of 5-(hydroxymethyl)-4,4-dimethyloxazolidin-2-one (50 mg, 0.34 mmol) in pyridine (1 mL) at −20° C. The mixture was allowed to stir for 15 minutes and then warmed to 60° C. for 1 hour. The mixture was concentrated under reduced pressure and the residue was purified by column chromatography on silica (20-100% ethyl acetate/hexanes) to afford 5-(chloromethyl)-4,4-dimethyloxazolidin-2-one. 1H NMR (500 MHz, CDCl3) δ 6.20 (br s, 1H), 4.38-4.35 (m, 1H), 3.75-3.70 (m, 1H), 3.62-3.57 (m, 1H), 1.42 (s, 3H), 1.31 (s, 3H). The mixture was concentrated under reduced pressure the residue was purified by column chromatography on silica (20-100% ethyl acetate/hexanes)