Dimethyl Sulfoxide → Biphenyl-2-ylcarbamic Acid 1-[2-(3-formylbenzylcarbamoyl)ethyl]piperidin-4-yl Ester

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Reaction Conditions

Reaction Steps

To a flask was added biphenyl-2-ylcarbamic acid 1-[2-(3-hydroxymethylbenzyl carbamoyl)ethyl]piperidin-4-yl ester (0.33 g, 0.68 mmol; prepared as described in Preparation 12), DCM (5 mL), DIPEA (0.47 mL, 2.7 mol) and DMSO (0.2 mL, 2.7 mol). Using an ice bath, the mixture was cooled to about −10° C. and sulfur trioxide pyridine-complex (0.32 g, 2.0 mol) was added. The reaction was stirred at −10° C. for 0.75 hour. Before removing the ice-bath, the reaction was quenched by adding water (5 mL). The aqueous layer was separated and the organic layer was washed with water (2×5 mL), 1.0N NaHSO4(aq) (2×5 mL), 1.0N NaHCO3(aq) (1×5 mL) and brine (0.5 L) and then dried over MgSO4 and filtered to provide the title compound which was used without further purification.

Provenance & Evidence