Trityl chloride → (4-Nitrophenyl)methyl (2S,4S)-2-cyano-4-[(triphenylmethyl)sulfanyl]pyrrolidine-1-carboxylate

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Reaction Steps

To a suspension of (2S,4S)-4-acetylthio-2-cyano-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (2.60 g) in a mixture of methanol (26 ml) and tetrahydrofuran (52 ml) was added a 28% solution of sodium methoxide in methanol (1.8 ml) at -10~-5° C. and the mixture was stirred at the same temperature for 30 minutes. To the mixture was added trityl chloride (2.20 g) at -10~-5° C., followed by stirring at the same temperature for 1 hour. The mixture was concentrated under reduced pressure to give a residue. The residue was dissolved in ethyl acetate, washed with water, dried over magnesium sulfate and concentrated under reduced pressure to give a syrup. The syrup was subjected to a column chromatography on silica gel (40 g) and eluted with dichloromethane to give (2S,4S)-2-cyano-1-(4-nitrobenzyloxycarbonyl)-4-tritylthiopyrrolidine (2.45 g).

Provenance & Evidence