Pyridine → (4R)-2-oxo-3-benzylthiazolidin-4-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

In 45 ml of dimethylsulfoxide was dissolved 20 g of (4R)-3-benzyl-4-hydroxymethylthiazolidin-2-one under room temperature, 1.45 ml of pyridine, 1.38 ml of trifluoroacetic acid, and 30 ml of ethyl acetate were added to the solution in this order. At 25° C., 22.2 g of dicyclohexylcarbodiimide and 15 ml of ethyl acetate were added to the above mixture, and the resulting mixture was stirred at 50° C. for 3 hours. To the reaction mixture was added 100 ml of ethyl acetate, the mixture was stirred at 10° C. or lower for 30 minutes, and precipitated product was filtered off. The filtrate was washed with brine (saturated brine:water=1:1), and the aqueous layer was further extracted with ethyl acetate. The organic layers were combined, washed with brine (saturated brine:water=1:1), dried, and concentrated to obtain (4R)-2-oxo-3-benzylthiazolidin-4-carbaldehyde.

Provenance & Evidence