Triphenylphosphine → HCID 22032581, compound

Participants

Reaction Steps

A solution of 1.01 g 2-fluoro-4-methylsulfanyl phenol (compound in Production Example D088), 1.28 g t-butyl 4-hydroxy-1-piperidinecarboxylate, 2.5 g triphenylphosphine and 4.2 g diethyl azodicarboxylate (40% toluene solution) in anhydrous tetrahydrofuran (30 mL) was heated for 8 hours under reflux in a stream of nitrogen. Water was added thereto, the reaction mixture was extracted with ethyl acetate, and the extract was dried over sodium sulfate and purified by silica gel chromatography (hexane/ethyl acetate) to give 1.41 g t-butyl 4-(2-fluoro-4-methylsulfanylphenoxy)piperidine-1-carboxylate. 5 mL of 4 N hydrogen chloride in ethyl acetate was added to this product and left for 1 hour. The solvent was removed, and the precipitated crystals were washed with ethyl acetate-ether to give 780 mg of the title compound as colorless crystals.

Provenance & Evidence