With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.872-32-2,2-Methyl-1-pyrroline,as a common compound, the synthetic route is as follows.
872-32-2, To a solution of i-Pr2NH (1.52 g, 2.1 mL, 15 mmol, 1.5 equiv) in anhyd THF (20 mL) was added n-BuLi (6 mL, 15 mmol, 1.5 equiv, 2.5 M in hexane) via a syringe at 0 ¡ãC under a nitrogen atmosphere, and the resulting solution was stirred for 30 min at 0 ¡ãC. Subsequently, 2-methyl-1-pyrroline (1; 0.83 g, 0.95 mL, 10 mmol, 1 equiv) was added via a syringe at 0 ¡ãC and the resulting solution was stirred for 1 h at 0 ¡ãC. Then, a solution of 1-benzyl-2-(bromomethyl)aziridine (2, R = Ph;8 2.25 g, 10 mmol, 1 equiv) in THF (10 mL) was added via a syringe at 0 ¡ãC and the resulting solution was stirred for 17 h at r.t. Afterwards, the reaction mixture was poured into H2O (50 mL) and extracted with Et2O (3 ¡Á 50 mL). Drying (MgSO4), filtration of the drying agent, and evaporation of the solvent in vacuo furnished 3a as an orange oil; yield: 2.12 g (9.3 mmol, 93percent). Because of the high purity of the obtained aziridines 3 (purity >95percent, 1H NMR), these compounds were used as such in the next step. IR (film): 2922, 1643, 1452, 732, 698 cm?1. 1H NMR (400 MHz, CDCl3): delta = 7.24?7.33 (m, 5 H), 3.75?3.80 (m, 2 H), 3.52 (d, J = 13.1 Hz, 1 H), 3.25 (d, J = 13.1 Hz, 1 H), 2.26?2.37 (m, 4 H), 1.78?1.87 (m, 3 H), 1.65 (d, J = 3.2 Hz, 1 H), 1.52?1.61 (m, 2 H), 1.43 (d, J = 6.2 Hz, 1 H). 13C NMR (100 MHz, CDCl3): delta = 177.7, 139.4, 128.31 (2 C), 128.28 (2 C), 127.0, 65.0, 60.8, 39.1, 37.3, 34.2, 31.4, 29.6, 22.5. MS (70 eV): m/z (percent) = 229 (M+ + 1, 100). HRMS (ESI): m/z calcd for C15H21N2: 229.1699 [M + H]+; found: 229.1703.
872-32-2 2-Methyl-1-pyrroline 70103, apyrrolines compound, is more and more widely used in various fields.
Reference£º
Article; Dolfen, Jeroen; D?hooghe, Matthias; Synthesis; vol. 49; 10; (2017); p. 2215 – 2222;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem