With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.6913-92-4,1-Benzyl-3-pyrroline,as a common compound, the synthetic route is as follows.
6913-92-4, Cycloaddition of the nitrone 7 on benzyl-3-pyrroline 2 in order to obtain the heterobicycle 8: The nitrone 7 (300 mg, 2.29 mmol) and benzyl-3-pyrroline 2 (0.8 ml, 4.20 mmol) are dissolved in toluene (3 ml) and stirred for 1 h at 80 C. with microwave irradiation. TLC (AcOEt/petroleum ether 1/3) shows total transformation of the nitrone. The solvent is then evaporated before purification of the cycloadduct 8 (390 ring, 58%) on a silica column (eluent: AcOEt/toluene 1/4) which removes the more polar compounds also formed. Aspect: colorless oil. Rf=0.4 (EtOAc/toluene 1/4). 1H NMR (500 MHz, CDCl3): delta 7.35-7.2 (m, 5H, H-Ar), 4.60 (dd, 1H, 3J=4.9 Hz, J=7.4 Hz, H-4), 4.20 (q, 2H, 3J=7.1 Hz, H-8, H-8?), 3.7 (d, 1H, 2J=13.2 Hz, H-11), 3.58 (d, 1H, 2J=13.2 Hz, H-11?), 3.24 (q, 1H, 3J=7.1 Hz, H-3), 3.16 (br s, 1H, H-6), 3.00 (d, 1H, 3J=11 Hz, H-5), 2.94 (d, 1H, 3J=9.8 Hz, H-2), 2.78 (s, 3H, NCH3), 2.28 (br s, 1H, H-2?), 2.19 (br s, 1H, H-5?), 1.27 (t, 3H, 3J=7.1 Hz, H-9) ppm. 13C NMR (126 MHz, CDCl3): delta 170.03 (C-7), 138.58, 128.73, 128.41, 127.17 (C-Ar), 81.03 (C-4), 75.48 (C-6), 61.26 (C-8), 59.08 (C-11), 58.77 (C-5), 56.79 (C-2), 52.54 (C-3), 43.85 (NCH3), 14.24 (C-9) ppm. HRMS ESI: m/z calcul. for C16H23N2O3 [M+H]+: 291.1703. found: 291.1702.
The synthetic route of 6913-92-4 has been constantly updated, and we look forward to future research findings.
Reference£º
Patent; Praly, Jean-Pierre; Aouadi, Kaiss; Cecioni, Samy; Denoroy, Luc; Parrot, Sandrine; US2015/175537; (2015); A1;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem