Downstream synthetic route of 131685-53-5

131685-53-5, As the paragraph descriping shows that 131685-53-5 is playing an increasingly important role.

131685-53-5, (R)-(-)-4-Benzyl-3-propionyl-2-oxazolidinone is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

TiCl3(OiPr) was first prepared using dry glassware under N2. A solution of 1 M TiCl4 in dichloromethane (3.4 mmol, 3.4 mL) was cooled to 0 C, and Ti(OiPr)4 (1.1 mmol, 0.34 mL) was added dropwise over 5 min. The solution was diluted with anhydrous dichloromethane (3.5 mL) and stirred at 0 C for 15 min. Meanwhile, compound 25a (1.0 g, 4.3 mmol) was dissolved in anhydrous dichloromethane (14 mL) in dry glassware under N2, and DIEA (0.79 mL) was added dropwise over 5 min, with stirring, at room temperature and then cooled to 0 C. The TiCl3(OiPr) solution was added to the 25a solution dropwise over 25 min. The TiCl3(OiPr) flask was rinsed with anhydrous dichloromethane (2 mL), and the rinse added to the combined flask. The solution was stirred at 0 C for 30 min, and then acrylonitrile (0.43 mL, 6.5 mmol) was added dropwise over 10 min, and this solution stirred at 0 C for 4 h. The reaction was quenched with the addition of saturated NH4Cl (25 mL) and H2O (15 mL), and the aqueous layer was extracted with diethyl ether (3 ¡Á 40 mL). The organic extracts were combined and washed with saturated NaHCO3 (55 mL) followed by brine (55 mL), dried over MgSO4 and concentrated in vacuo to yield a yellow oil. The oil was purified using the Flash+ system and a mobile phase of 3:7 ethyl acetate-hexanes (Rf = 0.30), to yield 26a as a very slightly yellow oil (890 mg, 72% yield). 1H NMR (500 MHz, CDCl3): delta 7.35 (dd, J1 = 7.6 Hz, J2 = 7.1 Hz, 2H), 7.30 (d, J = 7.3 Hz, 1H), 7.21 (d, J = 7.1 Hz, 2H), 4.69 (m, 1H), 4.20 (m, 2H), 3.83 (sextet, J = 6.9 Hz, 1H), 3.31 (dd, J1 = 13.4 Hz, J2 = 3.2 Hz, 1H), 2.78 (dd, J1 = 13.3 Hz, J2 = 3.6 Hz, 1H), 2.41 (dt, J1 = 7.7 Hz, J2 = 1.2 Hz, 2H), 2.19 (m, 1H), 1.81 (m, 1H), 1.24 (d, J = 6.9 Hz, 3H).

131685-53-5, As the paragraph descriping shows that 131685-53-5 is playing an increasingly important role.

Reference£º
Article; Girnys, Elizabeth A.; Porter, Vanessa R.; Mosberg, Henry I.; Bioorganic and Medicinal Chemistry; vol. 19; 24; (2011); p. 7425 – 7434;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem