With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.31886-58-5,(R)-(+)-N,N-Dimethyl-1-ferrocenylethylamine,as a common compound, the synthetic route is as follows.
For a preparation of Ugi amine 7 refer to Marquarding, D. et al., J. Am. Chem. Soc. 1970, 92, 5389.In a 200 ml schlenk tube, Ugi amine 7 (4 g, 15 mmol) was dissolved in Et2O (50 ml) at room temperature, n-BuLi (12 ml, 30 mmol) was added to the mixture at that temperature and stirred overnight under an inert atmosphere. The reaction mixture was cooled to -78C and Iodine (9.52 g, 37.5 mmol) dissolved in THF (60 ml) was added over the course of 10 min. The reaction was stirred at -78C for 90 min before allowing to warm to room temperature, at which point it was allowed to stirred for an additional 90 min before quenching at 0C with sodium thiosulfate(aq)(50 ml, 25% w/v). Dilute with Et2O (30 ml), the layers were separated and the aqueous layer was further extracted with ether (50 ml x 3). The combined organic fractions were dried over MgSO4solvent remove in vacuo and purified via flash column chromatography (5% MeOH, 5% TEA in DCM) to yield product (3.18 g, 55%).1H NMR (400 MHz, CDCl3) delta 4.46 (dd, J = 2.4, 1.4 Hz, 1 H), 4.24 (t, J = 2.6 Hz, 1 H), 4.15 (dd, J = 2.7, 1.3 Hz, 1 H), 4.12 (s, 5H), 3.62 (q, J = 6.8 Hz, 1 H), 2.15 (s, 6H), 1.50 (d, J = 6.8 Hz, 3H).13C NMR (101 MHz, CDCl3) delta 90.21 (ipso Cp), 74.32 (Fc), 71.67 (Fc), 68.19 (Fc), 65.59 (Fc), 57.59 (CH*), 45.49 (ipso Cp), 41.22 (CH3), 16.01 (CH3). MS (ES) (m/z) calcd for d4H18N56Fel 382.9833, found 382.9820. IR (cm-1): 3078 (=C-H), 2931 (CH2), 2878 (CH2), 2809 (CH2), 1446 (CH3), 1371 (CH3), 1243, 1087, 821 (CH=CH), 732 (CH Ar). Mp: melt at 58C-60C. aD(c = 0.0022 g/ml, DCM) = +7.3.
31886-58-5 (R)-(+)-N,N-Dimethyl-1-ferrocenylethylamine 16212257, achiral-nitrogen-ligands compound, is more and more widely used in various.
Reference£º
Patent; THE UNIVERSITY OF BIRMINGHAM; TSELEPIS, Chris; TUCKER, James; NGUYEN, Huy Van; HODGES, Nikolas John; MEHELLOU, Youcef; WO2015/92432; (2015); A1;,
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