反应详情

To a solution of (4R,5R)-4-Fluoromethyl-5-(4-methanesulfinyl-phenyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (1.0 g, 2.69 mmol) in DCM (50 mL) is cooled to 0° C. followed by addition of SbCl3 (0.018 g, 0.081 mmol) and DAST (0.6 mL, 4.582 mmol). The resulting reaction mixture is stirred at RT for 16 h. After completion reaction mixture is quenched with aqueous bicarbonate solution and extracted with ethyl acetate. Organic layer is dried over sodium sulphate, concentrated and purified by combi-flash chromatography (12 g column) using 8% ethyl acetate in n-Hexane as an eluent to afford title compound (564 mg) as colorless oil. 1H-NMR (400 MHz, DMSO): δ 1.41 (s, 9H), 1.48 (s, 3H), 1.61 (s, 3H), 377-.382 (m, 1H), 4.42-4.53 (m, 1H), 4.76-4.92 (m, 1H), 5.06 (d, J=7.36 Hz, 1H), 5.99 (d, J=52.32 Hz, 2H), 7.46-7.51 (m, 4H). LC-MS (m/z): M+H=374.1.

1. customThe resulting reaction mixture
2. customAfter completion reaction mixture
3. customis quenched with aqueous bicarbonate solution
4. extractionextracted with ethyl acetate
5. dry with materialOrganic layer is dried over sodium sulphate
6. concentrationconcentrated
7. custompurified by combi-flash chromatography (12 g column)