Potassium Carbonate → (4R,5R)-4-Fluoromethyl-5-(4-methanesulfinyl-phenyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

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Reaction Conditions

Reaction Steps

To a solution of (4R,5R)-4-Fluoromethyl-2,2-dimethyl-5-(4-methylsulfanyl-phenyl)-oxazolidine-3-carboxylic acid tert-butyl ester (6 g, 16.91 mmol) in ethanol (300 mL) is cooled to 0° C. followed by addition of K2CO3 (4.665 g, 33.80 mmol) and m-CPBA (2.90, 16.90 mmol) at 0° C. and resulting reaction mixture is stirred at 0° C. for 10 h. After completion, reaction mixture is quenched with water and extracted with ethyl acetate. Organic layer is dried over sodium sulphate, concentrated and purified by CombiFlash using 120 g column with 100% ethyl acetate in hexane as an eluent to afford title compound (4 g) as colorless oil. 1H-NMR (400 MHz, DMSO): δ 1.43 (s, 9H), 1.50 (s, 3H), 1.62 (s, 3H), 2.74 (s, 3H), 3.82-3.89 (m, 1H), 4.46-4.57 (m, 1H), 4.81 (m, 1H), 5.15 (d, J=7.28 Hz, 1H), 7.65-7.72 (m, 4H). LC-MS (m/z): M+H=372.3.

Provenance & Evidence