Triphenylphosphine → 2-(2-Acetylsulfanylethyl)-piperidine-1-carboxylic acid benzyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of triphenylphosphine (3.99 g in 35 mL dry tetrahydrofuran) was added 3.0 mL diisopropyl azodicarboxylate and the mixture stirred at 0° C. for 30 minutes. At this time, 2.0 g of 2-(2-hydroxyethyl)-piperidine-1-carboxylic acid benzyl ester was added followed by the dropwise addition of a solution of 1.16 g thioacetic acid in 19 mL tetrahydrofuran. After 2 hours, the mixture was concentrated in vacuo and purified by flash chromatography on silica gel (hexane:methylene chloride, 1:1) to give the title compound.

Provenance & Evidence