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.
Preparation of the Compound I.1: (alphaS,3R,4S) 4-hydroxy alpha-amino acetic 3-pyrrolidine acid or (alphaS,3R,4S) alpha-amino-(4-hydroxy-pyrrolidin-3-yl)acetic acid Cycloaddition of the nitrone 1 (corresponding to the compounds of formula (III)) on commercial N-Bn-3-pyrroline 2 (corresponding to the compounds of formula (IV)): synthesis of 3 (corresponding to the compounds of formula (II)): The nitrone 1 (392 mg, 1.64 mmol) [24, 25] and commercial N-Bn-3-pyrroline 2 in excess (314 mg, 1.97 mmol, 1.2 equiv.) are introduced into a flask adapted to a Biotage Initiator microwave reactor. After having filled the flask with argon, 2.5 ml of anhydrous toluene are poured therein. The flask, sealed with a septum and mounted in the microwave apparatus is irradiated with the instruction of maintaining a temperature of 140 C. for 2 h in order to totally convert the nitrone 1. Once the flask is cooled, the reaction crude product is concentrated and then purified by flash chromatography on a silica column (ethyl acetate) in order to lead to the cycloadduct 3 (625 mg, 1.57 mmol) with a yield of 96% and total stereoselectivity (the reaction was conducted on a scale of 5 grams with similar results). Single crystals of the compound 3 were obtained from a diethyl ether solution saturated with 3, left in the cold (freezer). Rf=0.48 (EtOAc). [alpha]D=+40.4 (c 1.1, CH2Cl2). 1H NMR (400 MHz, CDCl3): delta 7.37-7.20 (m, 5H, CH-ar), 4.59 (td, J=7.0 Hz, J=3.0 Hz, 1H, H-4), 3.71-3.49 (m, 3H, NCH2Ph, H-6), 3.42 (dd, J=10.3 Hz, J=6.6 Hz, 1H, H-3), 2.78 (dd, J=10.3 Hz, J=3.0 Hz, 1H, H-5), 2.75-2.69 (m, 4H, NCH3, H-2), 2.65 (dd, J=9.4 Hz, J=3.7 Hz, 1H, H-2′, 2.58 (dd, J=9.9 Hz, J=6.6 Hz, 1H, H-5′, 2.14-2.08 (m, 1H, H-9), 2.00 (dtt, J=12.9 Hz, J=6.5 Hz, J=3.3 Hz, 1H, H-10), 1.90-1.78 (m, 2H, H-11, H-12), 1.68-1.59 (m, 1H, H-12′), 1.48 (dt, J=13.5 Hz, J=6.7 Hz, 1H, H-15), 1.38 (dd, J=12.1 Hz, J=3.2 Hz, 1H, H-13), 1.18 (t, J=12.3 Hz, 1H, H-9′), 0.95-0.85 (m, 10H, H-11′, H-14, H-16) ppm. 13C NMR (100 MHz, CDCl3): delta 172.8 (C=O), 138.9 (CIV-ar), 128.6 (CH-ar), 128.3 (CH-ar), 127.1 (CH-ar), 88.0 (C-8), 79.6 (C-4), 71.9 (C-6), 59.6 (NCH2Ph), 59.4 (C-5), 59.3 (C-2), 49.1 (C-3), 48.2 (C-13), 41.0 (C-9), 35.0 (C-11), 29.0 (C-10), 25.9 (NCH3), 24.5 (C-15), 24.2 (CH3), 22.6 (C-12), 22.4 (CH3), 18.7 (CH3) ppm. HR-ESI-QToF MS (positive method): m/z calcul. for C24H36N3O2 [M+H]+ 398.2802. found 398.2806.
6913-92-4 1-Benzyl-3-pyrroline 561506, apyrrolines compound, is more and more widely used in various.
Reference£º
Patent; Praly, Jean-Pierre; Aouadi, Kaiss; Cecioni, Samy; Denoroy, Luc; Parrot, Sandrine; US2015/175537; (2015); A1;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem