Dimethyl Sulfoxide → 1,1-Dimethylethyl 3-formyl-3-methyl-1-piperidinecarboxylate

Participants

Reaction Steps

To an ice water cooled solution of tert-butyl 3-(hydroxymethyl)-3-methyl-1-piperidinecarboxylate (1.5 g, 6.6 mmol) in CH2Cl2 were added DMSO (7.1 g, 91.6 mmol), Et3N (5.5 mL, 39.8 mmol), and sulfur trioxide-Pyridine complex (3.1 g, 19.9 mmol) successively. The mixture was stirred at room temperature for 1 hr. The reaction mixture was diluted with ether, purified by column chromatography on silica gel (hexane:ethyl acetate, 5:1-4:1) to give tert-butyl 3-formyl-3-methyl-1-piperidinecarboxylate as a colorless oil form (1.3 g, yield; 86%).

Provenance & Evidence