With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.95530-58-8,(R)-4-Isopropyloxazolidin-2-one,as a common compound, the synthetic route is as follows.,95530-58-8
A 2.5M solution of n-butyllithium in hexanes (34.0mL, 85mmol) was added dropwise at -78C to a solution of (4R)-isopropyloxazolidinone (10.0g, 77mmol) in anhydrous THF (100mL). The mixture was stirred at -78C for 15min, and freshly distilled tiglyl chloride (9.3mL, 85mmol), prepared from tiglic acid and SOCl2, was added dropwise to the mixture. The mixture was stirred for 30minat -78C and slowly warmed up to 0C. After 15minat 0C, the mixture was quenched with a satd NH4Cl aqsolution (20mL). The organic solvents were evaporated and the mixture was extracted with AcOEt (50mL¡Á3). The combined extract was washed with brine (30mL), dried over MgSO4, concentrated, and purified by column chromatography (Petroleum ether/ethyl acetate=10:1). Compound 1 was obtained as a white solid (15.5g, 95%); mp 62-63C. Rf (Petroleum ether/ethyl acetate=10:1) 0.40. [alpha]D20 -91.2 (c 0.13, CHCl3). [lit.:20 its enantiomer, mp 63-64C. [alpha]D30 +91.8 (c 0.07, CHCl3)]. 1H NMR (400MHz, CDCl3) delta 6.21 (q, J=6.8Hz, 1H), 4.58-4.46 (m, 1H), 4.32 (dd, J=8.9, 8.9Hz, 1H), 4.17 (dd, J=8.9, 5.6Hz, 1H), 2.42-2.28 (m, 1H), 1.91 (s, 3H), 1.81 (d, J=8.9Hz, 3H), 0.92 (d, J=7.1Hz, 3H), 0.91 (d, J=6.6Hz, 3H). ESI-MS: Calcdfor C11H18NO3+ [M+H]: 212.1, found:
As the paragraph descriping shows that 95530-58-8 is playing an increasingly important role.
Reference£º
Article; Xu, Qian-Qian; Zhao, Qun; Shan, Guang-Sheng; Yang, Xi-Cheng; Shi, Qi-Yuan; Lei, Xinsheng; Tetrahedron; vol. 69; 50; (2013); p. 10739 – 10746;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem