反应详情

温度

-78 °C

To a solution of (4R,5R)-4-Fluoromethyl-5-(4-fluoromethylsulfanyl-phenyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (2.67 g, 7.158 mmol) in DCM (250 mL) is cooled to −78° C. followed by addition of solution of m-CPBA (1.59 g, 7.158 mmol) in DCM (25 mL). Reaction mixture is allowed to stir −78° C. for 20 minutes. After completion of the reaction mixture is quenched with aqueous bicarbonate solution and extracted with DCM. Organic layer is dried over sodium sulphate, concentrated and purified by combi-flash chromatography (40 g column) using 78% ethyl acetate in hexane as an eluent to afford title compound (1.88 g) as colorless oil. 1H-NMR (400 MHz, DMSO): δ 1.42 (s, 9H), 1.50 (s, 3H), 1.62 (s, 3H), 383-.388 (m, 1H), 4.46-4.58 (m, 1.5H), 4.75-4.84 (m, 1.5H), 5.17 (d, J=7.2 Hz, 1H), 5.25-5.27 (dd, J=1.12 Hz, J=8.8 Hz, 0.5H), 5.37-5.39 (m, 0.5H), 5.51-5.54 (dd, J=2.44 Hz, J=8.84 Hz, 0.5H), 5.63-5.64 (m, 0.5H), 7.70-7.77 (m, 4H). LC-MS (m/z): M+H=390.4.

1. customReaction mixture
2. customAfter completion of the reaction mixture is quenched with aqueous bicarbonate solution
3. extractionextracted with DCM
4. dry with materialOrganic layer is dried over sodium sulphate
5. concentrationconcentrated
6. custompurified by combi-flash chromatography (40 g column)