Extracurricular laboratory: Synthetic route of 31886-58-5

As the rapid development of chemical substances, we look forward to future research findings about 31886-58-5

(R)-(+)-N,N-Dimethyl-1-ferrocenylethylamine, cas is 31886-58-5, it is a common heterocyclic compound, the chiral-nitrogen-ligands compound, its synthesis route is as follows.,31886-58-5

The compound having the structure shown in Formula (II) of FIG. 4 was made using the scheme set forth in FIG. 1. First, alpha-Dimethylaminoethylferrocene, (14.30 g, 55.61 mmol), (as Compound 1) was dissolved in solvent (85 ml) under argon. N-butyl lithium (1.6 M) was added slowly (22.6 ml, 66.73 mmol, 1.2 eq.) and the reaction was stirred at room temperature for one hour. The solution was then purged with argon for thirty minutes. Chlorodiphenylphosphine (12.0 ml, 66.73 mmol, 1.2 eq.) in tert-butyl methyl ether (10 ml) was added slowly, and the reaction stirred at room temperature for four hours. The reaction was cooled to 0 C., and saturated sodium bicarbonate solution (57 ml) was added followed by water (45 ml). The composition separated into aqueous and organic phases, and the aqueous layer was removed and washed with toluene, and the resulting toluene was separated from the aqueous layer and combined with the organic layer, with the resulting composition being was dried over magnesium sulfate. The magnesium sulfate hydrate was then removed by filtration. The resulting filtrate solution was concentrated under vacuum to give an orange oil. The resulting oil was dissolved in ethanol and then solvents were removed under vacuum once more. The oil was then recrystallized by dissolving in the minimum amount of hot ethanol (45 ml) and cooling to room temperature. The resulting product, present as an orange solid, contained compound 2, which was 1-alpha-dimethyl-aminoethyl-2-(diphenylphosphino)ferrocene (9.16 g, 20.7 mmol, 31% yield).

As the rapid development of chemical substances, we look forward to future research findings about 31886-58-5

Reference£º
Patent; Eastman Chemical Company; How, Rebecca; Clarke, Matt; Hembre, Robert Thomas; Ponasik, James A.; Tolleson, Ginette S.; (17 pag.)US9308527; (2016); B2;,
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis