Pyridine → benzyl (2S)-2-formyl-2-methylpyrrolidine-1-carboxylate

Participants

Reaction Steps

To a solution obtained by dissolving 377 mg of the compound [63-2] and 147 mg of pyridine in 7.5 mL of chloroform, 673 mg of Dess-Martin periodinane was added at room temperature, and the mixture was heated under reflux for 1 hour. To the reaction solution, a saturated aqueous sodium thiosulfate solution was added, and the mixture was extracted with chloroform. The obtained organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine, sequentially, and dried over anhydrous sodium sulfate. The insolubles were filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate 100/0 to 60/40) to obtain 346 mg of benzyl (2S)-2-formyl-2-methylpyrrolidine-1-carboxylate [63-3] (hereinafter, referred to as the compound [63-3].

Provenance & Evidence