With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.108149-63-9,(R)-tert-Butyl 4-(hydroxymethyl)-2,2-dimethyloxazolidine-3-carboxylate,as a common compound, the synthetic route is as follows.
To a dry THF solution (30 mL) of alcohol 2 (3 g, 12.97 mmol) was addedNaH (0.985 g of 60% dispersion in mineral oil, 24.64 mmol) and then MeI wasadded drop wise (1.6 mL, 25.94 mmol), and the mixture was stirred at roomtemperature for 30 min. After the reaction was complete (TLC), it was cooled onan ice bath and quenched by slowly adding cold water (30 mL). The mixture wasextracted with dichloromethane (3 X 40 mL). The combined organic layers weredried over anhydrous Na2SO4.After concentration of the combined organic layers,the residual oil was subjected to flash chromatography (CombiFlash Rf 200i, Teledyne Isco) using RediSep silica gel column (12 g) eluting with petroleumether-EtOAc (9:1, isocratic) to furnish methyl ether 3 as a colourless liquid (2.8 g, 88%); Rf0.35(10% EtOAc in petroleum ether); [alpha]D25 -46.6 (c 1.03, CHCl3) [Lit. [alpha]D25-42.4 (c 1.37, CHCl3)10]; IR (CHCl3) umax: 3370, 3017, 2934, 1688,1464, 1387, 1252, 1217, 1168, 1095, 1030, 851, 766, 668 cm-1; 1HNMR (400 MHz, CDCl3) delta: 4.04-3.88 (m, 3H), 3.50 (m, 1H), 3.37(s, 3H), 3.34-3.26 (m, 1H), 1.61-1.44 (m, 15H); 13C NMR (100 MHz, CDCl3) delta: 152.2,151.7, 93.7, 93.3, 80.3, 79.8, 72.1, 71.3, 65.6, 65.3, 59.0, 58.9, 56.3, 56.1,28.4, 28.4, 27.5, 26.7, 24.3, 23.0; HRMS (ESI): m/zcalcd for C12H23NO4Na [M + Na]+268.1519; found: 268.1506.
108149-63-9, 108149-63-9 (R)-tert-Butyl 4-(hydroxymethyl)-2,2-dimethyloxazolidine-3-carboxylate 11053464, aoxazolidine compound, is more and more widely used in various fields.
Reference£º
Article; Aratikatla, Eswar K.; Bhattacharya, Asish K.; Tetrahedron Letters; vol. 56; 42; (2015); p. 5802 – 5803;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem