As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO306,mainly used in chemical industry, its synthesis route is as follows.,1273-86-5
Cyanuric chloride (TCT)(0.184g, 1mmol) was added intoa 50mL one-necked round-bottom flask with 10mL dry THF.The mixture was stirred in a cold bath and ferrocenemethanol(0.864g, 4mmol) in 10mL dry THF was slowly added tothe reaction system using a syringe. The mixture was stirred in the cold bath for 30min. Subsequently, DMAP (0.366g,3mmol) in 10mL dry THF was also slowly added to the reactionsystem using a syringe. The mixture was stirred in thecold bath for an additional 30min. Then, the temperature naturally rose to room temperature and was stirred for 8h.This time, the reaction system was refluxed. After the completion of the reaction indicated by simple TLC analysis, the solvent was evaporated under the reduced pressure, and theresidual was directly purified by column chromatography(EtOAc/Petroleum ether: 5:12:1) to obtain the target compound 1. 0.506g, light yellow solid, yield, 70%, Mp.:199-201 oC, 1H NMR(400MHz, CDCl3) (ppm): 4.73(s, 6H,32H of C5H4), 4.38(s, 6H, 32H of C5H4), 4.15(s, 15H,3C5H5), 4.10(s, 6H, 3CH2); 13C NMR(100MHz, CDCl3) (ppm): 148.7(3C=N), 81.5(6C), 70.4(6C), 68.7(15C),68.5(3C), 42.1(3CH2); ESI-MS(m/e, 100%) 746([M+23]+,100); Anal.calcd. for C36H33N3O3Fe3: N, 5.81; C, 59.75; H,4.56; Found: N, 5.75; C, 59.57 ; H, 4.64
With the synthetic route has been constantly updated, we look forward to future research findings about Ferrocenemethanol,belong iron-catalyst compound
Reference£º
Article; Yong, Jianping; Wu, Xiaoyuan; Liao, Jianzhen; Lu, Canzhong; Liu, Xiaolong; Medicinal Chemistry; vol. 12; 5; (2016); p. 426 – 431;,
Iron Catalysis in Organic Synthesis | Chemical Reviews
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion