Triphenylphosphine → HCID 57063518, compound

Participants

Reaction Steps

To a solution of (2R,4R)-1-allyloxycarbonyl-4-hydroxy-2-(2-pyridylmethyl) pyrrolidine (1.0 g), thiobenzoic acid (973 μl) and triphenylphosphine (1.30 g) in tetrahydrofuran (20 ml) was added dropwise diethyl azodicarboxylate (1.2 ml) at 0° C. The reaction mixture was stirred for 30 minutes, and then diluted with water and ethyl acetate. The aqueous layer was separated and extracted twice with ethyl acetate. The combined organic layer was washed with water (twice) and brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was column chromatographed on silica gel to give (2R,4S)-1-allyloxycarbonyl-4-benzoylthio-2-(2-pyridylmethyl)pyrrolidine (1.34 g).

Provenance & Evidence