6913-92-4,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.
N-Benzyl-3-pyrroline 2 (504 muL, 2.64 mmol) was added to a solution of ethyl chlorooximidoacetate (1 g, 6.62 mmol, 2.5 eq) in toluene (20 mL). The flask was heated to 110 C (oil bath) while a solution of Et3N (276.8 muL, 19.8 mmol, 7.5 eq) in toluene (15 mL) was added over 16 hh using a syringe pump. After concentration under reduced pressure, the crude product was purified by silica gel column chromatography (4:1 petroleum ether/EtOAc) to afford compound (+-)-20 (370 mg, 1.35 mmol, 51%). Yellow oil Rf = 0.52 (7:3 petroleum ether/EtOAc). 1H NMR (400 MHz, CDCl3): delta 7.26 (m, 5H, phenyl), 5.20 (dd, 1H, J5,4 = 4.5 Hz, J3,4 = 9.6 Hz, H-4), 4.31 (2 complex q, 2H, J = 7.2 Hz, diastereotopic OCH2), 3.91 (dt, 1H, J2′,3 = 1.0 Hz, J2,3 = 7.1 Hz, J3,4 = 9.5 Hz, H-3), 3.68 (d, 1H, 2J = 13.3 Hz, NCH2Ph), 3.55 (d, 1H, 2J = 13.3 Hz, NCH2Ph), 3.24 (d, 1H, 2J = 11.2 Hz, H-5′), 3.19 (d, 1H, 2J = 9.9 Hz, H-2′), 2.44 (dd, 1H, J2,3 = 7.2 Hz, 2J = 9.8 Hz, H-2), 2.37 (dd, 1H, J5,4 = 4.6 Hz, 2J = 11.2 Hz, H-5), 1.31 (t, 3H, J = 7.2 Hz, Me). 13C NMR (100 MHz, CDCl3): delta 160.7, 152.2 (C=N, C=O), 137.8 (C-ar), 128.5 (2CH-ar), 128.2 (2CH-ar), 127.1 (1CH-ar), 87.4 (C-4), 61.9 (OCH2), 61.1 (C-5), 58.3 (CH2 benzyl), 56.9 (C-2), 51.0 (C-3), 14.1 (CH3). MS m/z = 274.13 for C15H18N2O3; MS-ESI positive mode: 275.1 [M+H]+, 297.1 [M+Na]+.
The synthetic route of 6913-92-4 has been constantly updated, and we look forward to future research findings.
Reference£º
Article; Cecioni, Samy; Aouadi, Kaiss; Guiard, Julie; Parrot, Sandrine; Strazielle, Nathalie; Blondel, Sandrine; Ghersi-Egea, Jean-Francois; Chapelle, Christian; Denoroy, Luc; Praly, Jean-Pierre; European Journal of Medicinal Chemistry; vol. 98; (2015); p. 237 – 249;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem