1-(2-methyl-2-nitropropyl)pyrrolidine

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 18 ml of 2-nitropropane and 16.5 ml of pyrrolidine were dissolved in 60 ml of dioxan. 15 ml of aqueous formaldehyde solution (37%) and 8 ml of 2% sodium hydroxide solution were added at 5° C. The mixture was heated to 90° C. while stirring for 1 hour, cooled and thereafter extracted with 3×150 ml of ethyl acetate. Upon distillation in a water-jet vacuum, we obtained 19 g of 1-(2-nitro-2-methylpropyl)-pyrrolidine. cooled extracted with 3×150 ml of ethyl acetate Upon distillation in a water-jet vacuum, we

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Here, N-methyl-N-(2-methyl-2-nitro-propyl)-pyrrolidinium iodide was prepared by dissolving N-(2-methyl-2-nitro-propyl)-pyrrolidine (70 g, 0.4 mol) in toluene (100 mls), and thereafter under ice bath conditions adding drop wise methyl iodide (58 g, 26 mls, 0.41 mol) in toluene (70 mls) over a period of time of 30 minutes. After the addition was complete, the ice bath was removed and the solution was heated to a temperature of 80° C. A white solid was observed to precipitate. Stirring and heating were continued for an additional period of time of 6 hours. The white precipitate was recovered by filtration, and thereafter washed first with acetone (100 mls) and then with diethyl ether (50 mls) to yield after air drying 83 grams (65%), FTIR: (KBr, cm−1) 3026, 2978, 2874, 1544, 1492, 1475, 1459, 1439, 1377, 1344, 1307, 1229, 1195, 1152, 1052, 1012, 997, 926, 852, 833. 1H NMR (60 MHz, CDCl3/DMSO-d6, ref TMS, ppm) 1.85 (s, 6H) 2.1-2.3 (m, br, 4H) 2.96 (s, 2H) 3.9-3.7 (m, br, 4H) 4.45 (s, 3H). Elemental After the addition the ice bath was removed to precipitate heating The white precipitate was recovered by filtration washed first with acetone (100 mls) with diethyl ether (50 mls) to yield after air drying 83 grams (65%), FTIR

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Here, N-methyl-N-(2-methyl-2-nitro-propyl)-pyrrolidinium iodide was prepared by dissolving N-(2-methyl-2-nitro-propyl)-pyrrolidine (70 g, 0.4 mol) in toluene (100 mls), and thereafter under ice bath conditions adding drop wise methyl iodide (58 g, 26 mls, 0.41 mol) in toluene (70 mls) over a period of time of 30 minutes. After the addition was complete, the ice bath was removed and the solution was heated to a temperature of 80° C. A white solid was observed to precipitate. Stirring and heating were continued for an additional period of time of 6 hours. The white precipitate was recovered by filtration, and thereafter washed first with acetone (100 mls) and then with diethyl ether (50 mls) to yield after air drying 83 grams (65%), FTIR: (KBr, cm−1) 3026, 2978, 2874, 1544, 1492, 1475, 1459, 1439, 1377, 1344, 1307, 1229, 1195, 1152, 1052, 1012, 997, 926, 852, 833. 1H NMR (60 MHz, CDCl3/DMSO-d6, ref TMS, ppm) 1.85 (s, 6H) 2.1-2.3 (m, br, 4H) 2.96 (s, 2H) 3.9-3.7 (m, br, 4H) 4.45 (s, 3H). Elemental After the addition the ice bath was removed to precipitate heating The white precipitate was recovered by filtration washed first with acetone (100 mls) with diethyl ether (50 mls) to yield after air drying 83 grams (65%), FTIR

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 18 ml of 2-nitropropane and 16.5 ml of pyrrolidine were dissolved in 60 ml of dioxan. 15 ml of aqueous formaldehyde solution (37%) and 8 ml of 2% sodium hydroxide solution were added at 5° C. The mixture was heated to 90° C. while stirring for 1 hour, cooled and thereafter extracted with 3×150 ml of ethyl acetate. Upon distillation in a water-jet vacuum, we obtained 19 g of 1-(2-nitro-2-methylpropyl)-pyrrolidine. cooled extracted with 3×150 ml of ethyl acetate Upon distillation in a water-jet vacuum, we

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Here, N-methyl-N-(2-methyl-2-nitro-propyl)-pyrrolidinium iodide was prepared by dissolving N-(2-methyl-2-nitro-propyl)-pyrrolidine (70 g, 0.4 mol) in toluene (100 mls), and thereafter under ice bath conditions adding drop wise methyl iodide (58 g, 26 mls, 0.41 mol) in toluene (70 mls) over a period of time of 30 minutes. After the addition was complete, the ice bath was removed and the solution was heated to a temperature of 80° C. A white solid was observed to precipitate. Stirring and heating were continued for an additional period of time of 6 hours. The white precipitate was recovered by filtration, and thereafter washed first with acetone (100 mls) and then with diethyl ether (50 mls) to yield after air drying 83 grams (65%), FTIR: (KBr, cm−1) 3026, 2978, 2874, 1544, 1492, 1475, 1459, 1439, 1377, 1344, 1307, 1229, 1195, 1152, 1052, 1012, 997, 926, 852, 833. 1H NMR (60 MHz, CDCl3/DMSO-d6, ref TMS, ppm) 1.85 (s, 6H) 2.1-2.3 (m, br, 4H) 2.96 (s, 2H) 3.9-3.7 (m, br, 4H) 4.45 (s, 3H). Elemental After the addition the ice bath was removed to precipitate heating The white precipitate was recovered by filtration washed first with acetone (100 mls) with diethyl ether (50 mls) to yield after air drying 83 grams (65%), FTIR

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 18 ml of 2-nitropropane and 16.5 ml of pyrrolidine were dissolved in 60 ml of dioxan. 15 ml of aqueous formaldehyde solution (37%) and 8 ml of 2% sodium hydroxide solution were added at 5° C. The mixture was heated to 90° C. while stirring for 1 hour, cooled and thereafter extracted with 3×150 ml of ethyl acetate. Upon distillation in a water-jet vacuum, we obtained 19 g of 1-(2-nitro-2-methylpropyl)-pyrrolidine. cooled extracted with 3×150 ml of ethyl acetate Upon distillation in a water-jet vacuum, we