Triphenylphosphine → HCID 56639408, compound

Participants

Reaction Steps

(2S,4R)-1-(p-Nitrobenzyloxycarbonyl)-2-p-methoxybenzyloxycarbonylmethyl-4-hydroxypyrrolidine (1.40 g) and triphenylphosphine (1.18 g) were dissolved in 7 ml of dry tetrahydrofuran under nitrogen stream. To the resulting solution was added 783 mg of diethyl azodicarboxylate at 0° C., followed by stirring at the same temperature for 30 minutes. Thereafter, 342 mg of thioacetic acid was added thereto, and the mixture was stirred for 1 hour. The reaction mixture was diluted with ethyl acetate, washed successively with a saturated sodium bicarbonate solution and water, dried over anhydrous sodium sulfate and distilled to remove the solvent. The residue was purified by silica gel column chromatography to give (2R,4S)-1-(p-nitrobenzyl-oxycarbonyl)-2-p-methoxybenzyloxycarbonylmethyl-4-acetylthiopyrrolidine.

Provenance & Evidence