Tetrahydrofuran → (R)-tert-butyl 4-(3-hydroxypentan-3-yl)-2,2-dimethyloxazolidine-3-carboxylate

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A suspension of cerium (III) chloride (119 g, 482.07 mmol) in THF (350 mL) at room temperature was stirred vigorously for 2 hours. The suspension was cooled to −78° C. and ethylmagnesium bromide (482 mL, 482.07 mmol) was added dropwise. The mixture was stirred at −78° C. for 1.5 hours. (R)-3-tert-butyl 4-methyl 2,2-dimethyloxazolidine-3,4-dicarboxylate (Aldrich, 25 g, 96.41 mmol) in THF (100 mL) was then added dropwise at −78° C. The reaction was stirred at −78° C. for 30 minutes and then warmed to 0° C. for 15 minutes. The reaction was quenched with saturated NH4Cl, diluted further with water and extracted twice with ether. The organics were dried over magnesium sulfate, filtered and concentrated. Silica gel chromatography (0%-20% ethyl acetate/hexanes) afforded the title compound (26.4 g, 95%) as a colorless oil.

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