ethyl 3-methoxypropanimidate;hydrochloride

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Ethyl 3-methoxypropanimidate hydrochloride (1.0 g, 6.0 mmol) was suspended in DCM (12 mL) and cooled to 0° C. Pyridine (2 mL, 24.7 mmol) was added dropwise and the mixture was stirred for 15 min. Ethyl chloroformate (0.97 g, 9.0 mmol) was added dropwise and the mixture was diluted with DCM (20 mL), allowed to warm to RT, and stirred for 12 h. The mixture was diluted with a mixture of EtOAc and hexanes (1:1, 200 mL) and the solids were removed by filtration through a pad of diatomaceous earth. The filtrate was concentrated in vacuo to afford ethyl N-ethoxycarbonyl-3-methoxy-propanimidate (1.0 g, 83%) as a light green solid. 1H NMR (400 MHz, DMSO-d6): δ 4.08 (q, J=7.0 Hz, 2H), 4.05 (q, J=7.0 Hz, 2H), 3.50 (t, J=6.4 Hz, 2H), 3.19 (s, 3H), 2.57 (t, J=6.4 Hz, 2H), 1.20 (t, J=7.0 Hz, 3H), 1.19 (t, J=7.0 Hz, 3H). to warm to RT stirred for 12 h the solids were removed by filtration through a pad of diatomaceous earth The filtrate was concentrated in vacuo

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

実験手順: 3-Methoxypropanenitrile (5.0 g, 58.8 mmol) was dissolved in anhydrous ethanol (50 mL) under an atmosphere of Ar. The solution was cooled to 0° C., saturated with HCl gas, stirred for 6 h, allowed to warm to RT, and stirred for 6 h. The solvent was removed in vacuo. The residue was slurried with hexanes (50 mL) and sonicated for 10 min. The solids were allowed to settle and the solvent was removed by decantation. This was repeated (3×). The solid was collected and dried under high vacuum for 5 h to afford ethyl 3-methoxypropanimidate hydrochloride (6.2 g, 63%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 12.03 (br s, 1H), 11.22 (br s, 1H), 4.42 (q, J=7.0 Hz, 2H), 3.60 (t, J=5.9 Hz, 2H), 3.23 (s, 3H), 2.87 (t, J=5.9 Hz, 2H), 1.33 (t, J=7.0 Hz, 3H). stirred for 6 h The solvent was removed in vacuo sonicated for 10 min the solvent was removed by decantation The solid was collected dried under high vacuum for 5 h

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

実験手順: 3-Methoxypropanenitrile (5.0 g, 58.8 mmol) was dissolved in anhydrous ethanol (50 mL) under an atmosphere of Ar. The solution was cooled to 0° C., saturated with HCl gas, stirred for 6 h, allowed to warm to RT, and stirred for 6 h. The solvent was removed in vacuo. The residue was slurried with hexanes (50 mL) and sonicated for 10 min. The solids were allowed to settle and the solvent was removed by decantation. This was repeated (3×). The solid was collected and dried under high vacuum for 5 h to afford ethyl 3-methoxypropanimidate hydrochloride (6.2 g, 63%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 12.03 (br s, 1H), 11.22 (br s, 1H), 4.42 (q, J=7.0 Hz, 2H), 3.60 (t, J=5.9 Hz, 2H), 3.23 (s, 3H), 2.87 (t, J=5.9 Hz, 2H), 1.33 (t, J=7.0 Hz, 3H). stirred for 6 h The solvent was removed in vacuo sonicated for 10 min the solvent was removed by decantation The solid was collected dried under high vacuum for 5 h

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Ethyl 3-methoxypropanimidate hydrochloride (1.0 g, 6.0 mmol) was suspended in DCM (12 mL) and cooled to 0° C. Pyridine (2 mL, 24.7 mmol) was added dropwise and the mixture was stirred for 15 min. Ethyl chloroformate (0.97 g, 9.0 mmol) was added dropwise and the mixture was diluted with DCM (20 mL), allowed to warm to RT, and stirred for 12 h. The mixture was diluted with a mixture of EtOAc and hexanes (1:1, 200 mL) and the solids were removed by filtration through a pad of diatomaceous earth. The filtrate was concentrated in vacuo to afford ethyl N-ethoxycarbonyl-3-methoxy-propanimidate (1.0 g, 83%) as a light green solid. 1H NMR (400 MHz, DMSO-d6): δ 4.08 (q, J=7.0 Hz, 2H), 4.05 (q, J=7.0 Hz, 2H), 3.50 (t, J=6.4 Hz, 2H), 3.19 (s, 3H), 2.57 (t, J=6.4 Hz, 2H), 1.20 (t, J=7.0 Hz, 3H), 1.19 (t, J=7.0 Hz, 3H). to warm to RT stirred for 12 h the solids were removed by filtration through a pad of diatomaceous earth The filtrate was concentrated in vacuo

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

実験手順: 3-Methoxypropanenitrile (5.0 g, 58.8 mmol) was dissolved in anhydrous ethanol (50 mL) under an atmosphere of Ar. The solution was cooled to 0° C., saturated with HCl gas, stirred for 6 h, allowed to warm to RT, and stirred for 6 h. The solvent was removed in vacuo. The residue was slurried with hexanes (50 mL) and sonicated for 10 min. The solids were allowed to settle and the solvent was removed by decantation. This was repeated (3×). The solid was collected and dried under high vacuum for 5 h to afford ethyl 3-methoxypropanimidate hydrochloride (6.2 g, 63%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 12.03 (br s, 1H), 11.22 (br s, 1H), 4.42 (q, J=7.0 Hz, 2H), 3.60 (t, J=5.9 Hz, 2H), 3.23 (s, 3H), 2.87 (t, J=5.9 Hz, 2H), 1.33 (t, J=7.0 Hz, 3H). stirred for 6 h The solvent was removed in vacuo sonicated for 10 min the solvent was removed by decantation The solid was collected dried under high vacuum for 5 h