Sodium Iodide → 1-(tert-Butoxycarbonyl)-3-[[2-(4-chlorophenyl)-4-methylthiazol-5-yl]methoxymethyl]piperidine

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1-(tert-Butoxycarbonyl)piperidin-3-ylmethanol (215 mg, 1.00 mmol) was dissolved in tetrahydrofuran (5 mL). While this solution was chilled in an ice bath, 60% sodium hydride in oil (44.0 mg, 1.10 mmol) was added and the mixture was stirred for 20 min. Subsequently, 5-chloromethyl-2-(4-chlorophenyl)-4-methylthiazole (258 mg, 1.00 mmol) in tetrahydrofuran (5 mL) and sodium iodide (15.0 mg, 0.100 mmol) were added. The mixture was stirred for 2 hours while chilled in an ice bath and was further stirred for 6 hours at room temperature. Subsequently, ethyl acetate was added and the mixture washed sequentially with 5% aqueous citric acid and brine, followed by drying over magnesium sulfate and evaporation of the solvent. Purification of the resulting residue by silica gel column chromatography (hexane:ethyl acetate=20:1->5:1) gave 258 mg (59%) of the desired compound as a colorless oil.

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