Hydrochloric Acid → (2R,3R)-2-Styryl-tetrahydro-pyran-3-carboxylic acid

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Reaction Steps

To a stirring solution of (4R)-4-benzyl-3-[(2R,3R)-2-styryl-tetrahydro-pyran-3-carbonyl]-oxazolidin-2-one (177 mg, 0.453 mmol) in 4:1 tetrohydrofuran:water (2.27 mL) at 0° C. was added lithium hydroxide (17.3 mg, 0.724 mmol) dissolved in 900 μL of water. To the resulting solution was added 30 wt % aqueous hydrogen peroxide (205 μL) dropwise, and the now pale yellow solution was stirred for 30 min. The solution was then poured into water (50 mL) containing a 1.5 mL-aliquot of 1.3 M sodium sulfite, and the resulting aqeuous layer was acidified with 6N aqueous hydrogen chloride (10 mL). The aqueous layer was washed with ethyl acetate (3×50 mL), and the combined organic layers were washed with brine (15 mL), dried over sodium sulfate, and concentrated in vacuo. The resulting residue was purified by flash chromatography (SiO2, 33% ethyl acetate in hexanes) to yield the desired product 100 mg (95%) as a pale yellow oil. MS (ESI), m+/z: (M+H)+=233.2.

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