73286-71-2 N-Boc-2-pyrroline 10844857, apyrrolines compound, is more and more widely used in various.
73286-71-2, N-Boc-2-pyrroline is a pyrrolines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,73286-71-2
General procedure: To a stirred solution of p-chlorobenzaldehyde, 6 (1.16 g, 8.25 mmol) and aniline 5 (1.83 g, 8.23 mmol) in anhydrous CH3CN (30 mL), 4 A molecular sieves and Sc(OTf)3 (0.81 g, 1.65 mmol) were added. The mixture was stirred at room temperature under argon atmosphere for 5 min and then treated with a solution of enamine 4 (1.50 g, 8.01 mmol) in anhydrous CH3CN (16 mL). The resulting suspension was stirred at room temperature under argon atmosphere for 3 days. Then, the resulting mixture was diluted with sat. aq. NaHCO3 (150 mL) and extracted with EtOAc (3 * 200 mL). The combined organic extracts were dried over anhydrous Na2SO4 and evaporated under reduced pressure to give a solid residue (4.71 g), mainly consisting of a diastereomeric mixture of octahydrobenzonaphthyridines 7, which was used in the next step without further purification. To a solution of crude diastereomeric mixture 7 (4.58 g of a crude of 4.71 g) in anhydrous CHCl3 (150 mL), DDQ (4.85 g, 21.4 mmol) was added. The reaction mixture was stirred at room temperature under argon atmosphere overnight, diluted with CH2Cl2 (150 mL) and washed with sat. aq. NaHCO3 (3 * 250 mL). The combined organic extracts were dried over anhydrous Na2SO4 and evaporated under reduced pressure to give a solid residue (5.33 g), which was purified through column chromatography (35-70 mum silica gel, hexane/EtOAc mixtures, gradient elution). On elution with hexane/1-Benzyl-9-(tert-butoxycarbonylaminomethyl)-5-(4-chlorophenyl)-1,2,3,4-tetrahydro-2-oxobenzo[h][1,6]naphthyridine 8EtOAc 80:20, compound 8 (1.94 g, 47% yield) was isolated as a white solid; Rf 0.83 (hexane/EtOAc 1:1). A solution of 8 (30 mg, 0.06 mmol) in CH2Cl2 (5 mL) was filtered through a 0.2 mum PTFE filter and evaporated at reduced pressure. The solid was washed with pentane (3 * 5 mL) to give, after drying under standard conditions, the analytical sample of 8 (27 mg):
73286-71-2 N-Boc-2-pyrroline 10844857, apyrrolines compound, is more and more widely used in various.
Reference£º
Article; Di Pietro, Ornella; Vicente-Garcia, Esther; Taylor, Martin C.; Berenguer, Diana; Viayna, Elisabet; Lanzoni, Anna; Sola, Irene; Sayago, Helena; Riera, Cristina; Fisa, Roser; Clos, M. Victoria; Perez, Belen; Kelly, John M.; Lavilla, Rodolfo; Munoz-Torrero, Diego; European Journal of Medicinal Chemistry; vol. 105; (2015); p. 120 – 137;,
Pyrroline – Wikipedia
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