108149-63-9, (R)-tert-Butyl 4-(hydroxymethyl)-2,2-dimethyloxazolidine-3-carboxylate is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated
108149-63-9, General procedure: To a stirred solution of 35 (0.300g, 1.30mmol), appropriate hydroxypyridine (0.247g, 2.60mmol) and PPh3 (0.681g, 2.60mmol) in anhydrous THF (15mL) was added DIAD 95% (0.54mL, 2.60mmol) at 80C. After 3h, the mixture was concentrated under reduced pressure and EtOAc (100mL) was added. The organic layer was extracted with cold 0.1M aqueous HCl (2¡Á40mL). 1 M aqueous NaOH (60mL) was added to the aqueous layer and the resulting mixture was extracted with EtOAc (2¡Á100mL). The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by flash silica gel column chromatography eluting with Hexanes/EtOAc (7:3). 4.10.1 1,1-Dimethylethyl (S)-2,2-dimethyl-4-[[(3-pyridyl)oxy]methyl]-3-oxazolidinecarboxylate (15) Yellow oil. 53% yield: [alpha]D25+58 [alpha]D25+58 (c 3.46, CH2Cl2); IR v 3058, 2979, 2936, 2880, 1689, 1575, 1477, 1427, 1385, 1376, 1365cm-1; 1H NMR (200MHz, CDCl3) delta (ppm): 8.29-8.18 (m, 2H, Ar), 7.25-7.13 (m, 2H, Ar), 4.23-3.87 (m, 5H, CHN, CH2O, CH2OAr), 1.58, 1.53, 1.46 (s, 15H, CH3, C(CH3)3); 13C NMR (50MHz, CDCl3) delta (ppm) major rotamer: 154.57 (Ar), 152.21 (C=O), 142.07, 138.32, 123.71, 120.69 (Ar), 93.49 (C), 80.58 (C(CH3)3), 66.17, 65.00 (CH2O, CH2OAr), 55.79 (CHN), 28.29 (C(CH3)3), 27.41, 24.12 (CH3). HRMS (m/z): [MH+] calcd for C16H25N2O4, 309.1809; found, 309.1818.
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Reference£º
Article; Andrade, Saulo F.; Oliveira, Barbara G.; Pereira, Larissa C.; Ramos, Jonas P.; Joaquim, Angelica R.; Steppe, Martin; Souza-Fagundes, Elaine M.; Alves, Ricardo J.; European Journal of Medicinal Chemistry; vol. 138; (2017); p. 13 – 25;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem