4-Toluenesulfonyl chloride → 4-[3-(Toluene-4-sulfonyloxymethyl)furan-2-yl]-piperidine-1-carboxylic Acid t-Butyl Ester

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Reaction Conditions

Reaction Steps

4-(3-Hydroxymethylfuran-2-yl)piperidine-1-carboxylic acid t-butyl ester (0.3 g, 1.1 mmol, 1.0 eq.) was dissolved in DCM (5.7 mL). The mixture was cooled to 0° C. and DABCO (132 mg, 1.2 mmol, 1.1 eq.) was added, followed by TsCl (224 mg, 1.2 mmol, 1.1 eq.). The mixture was stirred at 0° C. for 90 minutes, then diluted with EtOAc (500 mL) and washed with water (2×250 mL). The organic layer was dried over anhydrous Na2SO4, filtered and concentrated by rotary evaporation to yield the title compound (233 mg), which was used without further purification.

Provenance & Evidence