Dimethyl Sulfoxide → tert-Butyl 4-formylpiperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

Dichloromethane solution of DMSO (2.4 mL, 33.4 mmol) was added to dichloromethane solution of oxalyl chloride (1.5 mL, 16.7 mmol) at −76° C. for 30 minutes. After stirring for 30 minutes at −78° C., dichloromethane solution (15 mL) of 4-(hydroxymethyl)piperidine-1-carboxilic acid tert-butyl ester (3.00 g, 13.9 mmol) was added at −76° C. for 30 minutes. After stirring for 30 minutes at −76° C., triethylamine (9.7 mL) was added at −76° C. for 10 minutes. The mixture was stirred at −76° C. for 15 minutes and was stirred for 45 minutes after increasing the temperature to room temperature. The reaction was terminated by adding water. The reaction mixture was extracted with dichloromethane three times. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane:ethyl acetate=3:1) to obtain compound P33 (2.41 g, 11.3 mmol, 81%).

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