951127-25-6, tert-Butyl ((2R,3S)-2-(2,5-difluorophenyl)-5-oxotetrahydro-2H-pyran-3-yl)carbamate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated
951127-25-6, General procedure: Compound 3 (101 mg, 0.31 mmol) and amines 10a-g (0.32 mmol) were dissolved in trifluoroacetic acid (0.45 mL, 6.1 mmol) at 0 C and stirred at 0 C for 1 h. To the resulting solution, DMAC (1.3 mL,14.0 mmol) and TEA (0.42 mL, 3.0 mmol) were added slowly and the internal temperature was maintained below 15 C. The mixture was then cooled to 0 C, treated with STAB (91 mg, 0.43 mmol),and stirred at 0-2 C for 5 h. Eventually the pH of the reaction was brought to 9 with conc. aq. NH3, and the resulting suspension was filtered. The filtrate was diluted with water (15 mL), extracted ethyl acetate for several times. Combined organic phases were dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography (SiO2, DCM: MeOH = 20:1) to yield the products11-14. From compound 10a (30 mg, 0.32 mmol), according to general procedure A, compound 11 (lightyellow oil, 61 mg, 0.20 mmol, 65 %) was obtained. Rf 0.6 (20:1, dichloromethane : methanol); [alpha]D -1.02(c 0.275, CHCl3); HPLC tR 2.63 min; 1H NMR (500 MHz, CDCl3) delta 7.23 – 7.13 (m, 3H, ArH), 7.05 – 6.95(m, 2H, ArH), 6.76 – 6.71 (m, 1H, ArH), 6.70 – 6.68 (m, 1H, ArH), 6.68 – 6.65 (m, 1H, ArH), 4.33 (ddd,J = 11.2, 4.6, 2.1 Hz, 1H, H-5), 4.25 (d, J = 9.4 Hz, 1H, H-1), 3.74 (tt, J = 10.9, 4.3 Hz, 1H, H-4), 3.14 (t,J = 10.9 Hz, 1H, H-5?), 2.97 – 2.91 (m, 1H, H-2), 2.52 (dtd, J = 12.1, 4.0, 2.3 Hz, 1H, H-3), 1.67 (s, 2H,NH2), 1.36 (q, J = 11.6 Hz, 1H, H-3), peaks of NH was missing; 13C NMR (151 MHz, CDCl3) delta 160.12 -158.35 (m, ArC), 157.52 – 155.64 (m, ArC), 146.67 (ArC), 129.61 (2C, ArC), 128.60 (dd, J C-C-F = 16.1,7.4 Hz, ArC), 118.03 (ArC), 116.68 (dd, J C-C-F = 25.6, 8.5 Hz, ArC), 116.37 (dd, J C-C-F = 24.2, 8.7 Hz,ArC), 114.83 (dd, J = 24.6, 4.2 Hz, ArC), 113.16 (2C, ArC), 79.35 (C-1), 72.09 (C-5), 53.20 (C-2), 49.08(C-4), 40.73 (C-3); HRMS (ESI+) calcd. For C17H19F2N2O+ 305.1460, found 305.1455.
The synthetic route of 951127-25-6 has been constantly updated, and we look forward to future research findings.
Reference£º
Article; Li, You; Liu, Tongchao; Li, Chungang; Xiong, Bing; Zhao, Dongmei; Cheng, Maosheng; Chen, Guohua; Shen, Jingkang; Chen, Yue-Lei; Synthetic Communications; vol. 47; 4; (2017); p. 357 – 363;,
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