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

Yield:130564-37-3 86.7%

Reaction Conditions:

with sodium hydroxide in water at 2550; for 2 h;

Steps:

1 Step 1:
Synthesis of 1-(2-methyl-2-nitropropyl)pyrrolidine


To a stirred solution of pyrrolidine (5.0 g, 70.42 mmol, 1.0 eq) and 2-nitropropane (6.33 ml, 70.42 mmol, 1.0 eq) at 10° C. dropwise slowly added formaldehyde (5.85 ml, 3.0 eq, 37%) and aqueous NaOH solution (3.0 mL, 0.5 N).
The reaction mixture was stirred at 25° C. for about 1 hour and then at 50° C. for about 1 hour.
The solution was diluted with water and extracted with diethyl ether.
The combined organic extracts were dried over Na₂SO₄, filtered and combined with HCl in dioxane (30 mL).
The precipitates formed were collected by filtration and dried in vacuo gave the desired product (10.5 g, yield: 86.7%) as a semisolid. ¹H NMR (CD₃OD, 300 MHz): δ ppm 3.16 (s, 2H), 2.67 (m, 4H), 1.37 (m, 4H), 1.21 (s, 6H); ESI-MS: m/z 173.09 (M+H)+.

References:

US2018/237472,2018,A1 Location in patent:Paragraph 0136; 0137