Pyridine → (1R,2R)-2-(4-Chloro-phenoxymethyl)-4-hydroxy-cyclopentanecarboxylic acid ethyl ester

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To a cold (ice bath) solution of (1R,2R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-(4-chloro-phenoxymethyl)-cyclopentanecarboxylic acid ethyl ester (epimeric mixture, 529 mg) in tetrahydrofuran (20 mL) was slowly added pyridine (8.1 g) and a pyridine-hydrofluoric acid complex (70% HF w/w, 9.07 g). The mixture was stirred 3 h at room temperature then solid sodium hydrogenocarbonate an aqueous saturated solution of sodium hydrogenocarbonate were added to adjust the pH to 7. The mixture was extracted with dichloromethane and the combined organic layers were washed with an aqueous saturated solution of sodium hydrogenocarbonate, dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel with a gradient of cyclohexane/ethylacetate (6:1 to 1:1 v/v) as eluant to afford the title compound (0.346 g, 90%) as a light yellow oil. MS (EI): 299.1 (M+H)+.

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