Hydrochloric Acid → HCID 57191012, compound

Participants

Reaction Steps

In methylene chloride (24 ml), oxalyl chloride (0.40 ml) was dissolved. To the resulting solution, a solution of dimethyl sulfoxide (0.44 ml) in methylene chloride (1.6 ml) was added at -78° C., followed by stirring for 10 minutes. To the resulting solution, a solution of (2S,4S)-2-hydroxymethyl-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (1 g) in methylene chloride (8 ml) was added dropwise at the same temperature, followed by stirring at -78° C. for 15 minutes and -50 to -60° C. for one hour. To the reaction mixture, triethylamine (2.4 ml) was added, followed by stirring at -14 to -15° C. for 20 minutes. To the reaction mixture, 1N hydrochloric acid was added to make the resulting solution acidic, followed by extraction with methylene chloride. The methylene chloride layer was washed with water and saline and then dried over anhydrous sodium sulfate. The solvent was distilled off, whereby (2S,4S)-2-formyl-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (1 g) was obtained.

Provenance & Evidence