N-methylcyclobutanamine

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of N-methylcyclobutanamine (1 g, 3.89 mmol) and potassium carbonate (1.18 g, 8.56 mmol) in acetonitrile (20 ml) at 0° C. was added 1-bromo-3-chloropropane (383 μl, 3.89 mmol). Reaction was warmed to room temperature and stirred for 24 hours. Solid removed by filtration and filtrate concentrated in vacuo to give the title compound (241 mg, 38%) as an oil. No purification was performed. LRMS APCI+ m/z 162 [MH]+. Reaction Solid removed by filtration and filtrate concentrated in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of N-methylcyclobutanamine (1 g, 3.89 mmol) and potassium carbonate (1.18 g, 8.56 mmol) in acetonitrile (20 ml) at 0° C. was added 1-bromo-3-chloropropane (383 μl, 3.89 mmol). Reaction was warmed to room temperature and stirred for 24 hours. Solid removed by filtration and filtrate concentrated in vacuo to give the title compound (241 mg, 38%) as an oil. No purification was performed. LRMS APCI+ m/z 162 [MH]+. Reaction Solid removed by filtration and filtrate concentrated in vacuo

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Combined a solution of tert-butyl 3-oxoazetidine-1-carboxylate (500 mg, 2.92 mmol) and N-methylcyclobutanamine (0.373 mL, 3.50 mmol) in methylene chloride (15 mL) and added sodium triacetoxyborohydride (929 mg, 4.38 mmol) and the solution stirred at 20° C. for 3 h. The solution was concentrated in vacuo to give a white solid. The solid was taken up in ethyl acetate (50 mL), washed with saturated sodium bicarbonate (50 mL) and brine, dried with magnesium sulfate, and concentrated in vacuo to give a residue which was purified on a 40 g silica gel column eluted with 0 to 70% ethyl acetate in hexanes to give the title compound (342 mg, 1.423 mmol, 48.7%) as a clear, colorless oil. 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.43 (s, 9 H) 1.60-1.75 (m, 2 H) 1.85-2.04 (m, 4 H) 2.07 (s, 3 H) 2.81-2.94 (m, 1 H) 3.27-3.30 (m, 1 H) 3.81-3.88 (m, 2 H) 3.88-3.97 (m, 2 H); MS: 241 (M+H). The solution was concentrated in vacuo to give a white solid washed with saturated sodium bicarbonate (50 mL) and brine dried with magnesium sulfate concentrated in vacuo to give a residue which was purified on a 40 g silica gel column eluted with 0 to 70% ethyl acetate in hexanes

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Combined a solution of tert-butyl 3-oxoazetidine-1-carboxylate (500 mg, 2.92 mmol) and N-methylcyclobutanamine (0.373 mL, 3.50 mmol) in methylene chloride (15 mL) and added sodium triacetoxyborohydride (929 mg, 4.38 mmol) and the solution stirred at 20° C. for 3 h. The solution was concentrated in vacuo to give a white solid. The solid was taken up in ethyl acetate (50 mL), washed with saturated sodium bicarbonate (50 mL) and brine, dried with magnesium sulfate, and concentrated in vacuo to give a residue which was purified on a 40 g silica gel column eluted with 0 to 70% ethyl acetate in hexanes to give the title compound (342 mg, 1.423 mmol, 48.7%) as a clear, colorless oil. 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.43 (s, 9H) 1.60-1.75 (m, 2H) 1.85-2.04 (m, 4H) 2.07 (s, 3H) 2.81-2.94 (m, 1H) 3.27-3.30 (m, 1H) 3.81-3.88 (m, 2H) 3.88-3.97 (m, 2H); MS: 241 (M+H). The solution was concentrated in vacuo to give a white solid washed with saturated sodium bicarbonate (50 mL) and brine dried with magnesium sulfate concentrated in vacuo to give a residue which was purified on a 40 g silica gel column eluted with 0 to 70% ethyl acetate in hexanes

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Combined a solution of tert-butyl 3-oxoazetidine-1-carboxylate (500 mg, 2.92 mmol) and N-methylcyclobutanamine (0.373 mL, 3.50 mmol) in methylene chloride (15 mL) and added sodium triacetoxyborohydride (929 mg, 4.38 mmol) and the solution stirred at 20° C. for 3 h. The solution was concentrated in vacuo to give a white solid. The solid was taken up in ethyl acetate (50 mL), washed with saturated sodium bicarbonate (50 mL) and brine, dried with magnesium sulfate, and concentrated in vacuo to give a residue which was purified on a 40 g silica gel column eluted with 0 to 70% ethyl acetate in hexanes to give the title compound (342 mg, 1.423 mmol, 48.7%) as a clear, colorless oil. 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.43 (s, 9H) 1.60-1.75 (m, 2H) 1.85-2.04 (m, 4H) 2.07 (s, 3H) 2.81-2.94 (m, 1H) 3.27-3.30 (m, 1H) 3.81-3.88 (m, 2H) 3.88-3.97 (m, 2H); MS: 241 (M+H). The solution was concentrated in vacuo to give a white solid washed with saturated sodium bicarbonate (50 mL) and brine dried with magnesium sulfate concentrated in vacuo to give a residue which was purified on a 40 g silica gel column eluted with 0 to 70% ethyl acetate in hexanes

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of N-methylcyclobutanamine (1 g, 3.89 mmol) and potassium carbonate (1.18 g, 8.56 mmol) in acetonitrile (20 ml) at 0° C. was added 1-bromo-3-chloropropane (383 μl, 3.89 mmol). Reaction was warmed to room temperature and stirred for 24 hours. Solid removed by filtration and filtrate concentrated in vacuo to give the title compound (241 mg, 38%) as an oil. No purification was performed. LRMS APCI+ m/z 162 [MH]+. Reaction Solid removed by filtration and filtrate concentrated in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of N-methylcyclobutanamine (1 g, 3.89 mmol) and potassium carbonate (1.18 g, 8.56 mmol) in acetonitrile (20 ml) at 0° C. was added 1-bromo-3-chloropropane (383 μl, 3.89 mmol). Reaction was warmed to room temperature and stirred for 24 hours. Solid removed by filtration and filtrate concentrated in vacuo to give the title compound (241 mg, 38%) as an oil. No purification was performed. LRMS APCI+ m/z 162 [MH]+. Reaction Solid removed by filtration and filtrate concentrated in vacuo

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Combined a solution of tert-butyl 3-oxoazetidine-1-carboxylate (500 mg, 2.92 mmol) and N-methylcyclobutanamine (0.373 mL, 3.50 mmol) in methylene chloride (15 mL) and added sodium triacetoxyborohydride (929 mg, 4.38 mmol) and the solution stirred at 20° C. for 3 h. The solution was concentrated in vacuo to give a white solid. The solid was taken up in ethyl acetate (50 mL), washed with saturated sodium bicarbonate (50 mL) and brine, dried with magnesium sulfate, and concentrated in vacuo to give a residue which was purified on a 40 g silica gel column eluted with 0 to 70% ethyl acetate in hexanes to give the title compound (342 mg, 1.423 mmol, 48.7%) as a clear, colorless oil. 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.43 (s, 9 H) 1.60-1.75 (m, 2 H) 1.85-2.04 (m, 4 H) 2.07 (s, 3 H) 2.81-2.94 (m, 1 H) 3.27-3.30 (m, 1 H) 3.81-3.88 (m, 2 H) 3.88-3.97 (m, 2 H); MS: 241 (M+H). The solution was concentrated in vacuo to give a white solid washed with saturated sodium bicarbonate (50 mL) and brine dried with magnesium sulfate concentrated in vacuo to give a residue which was purified on a 40 g silica gel column eluted with 0 to 70% ethyl acetate in hexanes

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Combined a solution of tert-butyl 3-oxoazetidine-1-carboxylate (500 mg, 2.92 mmol) and N-methylcyclobutanamine (0.373 mL, 3.50 mmol) in methylene chloride (15 mL) and added sodium triacetoxyborohydride (929 mg, 4.38 mmol) and the solution stirred at 20° C. for 3 h. The solution was concentrated in vacuo to give a white solid. The solid was taken up in ethyl acetate (50 mL), washed with saturated sodium bicarbonate (50 mL) and brine, dried with magnesium sulfate, and concentrated in vacuo to give a residue which was purified on a 40 g silica gel column eluted with 0 to 70% ethyl acetate in hexanes to give the title compound (342 mg, 1.423 mmol, 48.7%) as a clear, colorless oil. 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.43 (s, 9H) 1.60-1.75 (m, 2H) 1.85-2.04 (m, 4H) 2.07 (s, 3H) 2.81-2.94 (m, 1H) 3.27-3.30 (m, 1H) 3.81-3.88 (m, 2H) 3.88-3.97 (m, 2H); MS: 241 (M+H). The solution was concentrated in vacuo to give a white solid washed with saturated sodium bicarbonate (50 mL) and brine dried with magnesium sulfate concentrated in vacuo to give a residue which was purified on a 40 g silica gel column eluted with 0 to 70% ethyl acetate in hexanes

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of N-methylcyclobutanamine (1 g, 3.89 mmol) and potassium carbonate (1.18 g, 8.56 mmol) in acetonitrile (20 ml) at 0° C. was added 1-bromo-3-chloropropane (383 μl, 3.89 mmol). Reaction was warmed to room temperature and stirred for 24 hours. Solid removed by filtration and filtrate concentrated in vacuo to give the title compound (241 mg, 38%) as an oil. No purification was performed. LRMS APCI+ m/z 162 [MH]+. Reaction Solid removed by filtration and filtrate concentrated in vacuo