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

Participants

Reaction Conditions

Reaction Steps

To a solution of 1.75 mL (20 mmol) of oxalyl chloride in 20 mL of CH2Cl2 at −78° C. was added a solution of 2.13 mL (30 mmol) of DMSO in 5 mL of CH2Cl2 and the reaction mixture was stirred for 20 min at −78° C. To this reaction mixture was then added a solution of 2.41 g (11.2 mmol) of 1-t-butoxycarbonyl-4-hydroxymethylpiperidine in 10 mL of CH2Cl2. After stittring for 30 min, 7 mL of Et3N was then added and the reaction mixture was allowed to slowly warm to rt and stirred at rt for 1 h. To the reaction mixture was added 50 mL of H2O and the mixture was extracted with CH2Cl2. The combined organic fractions were washed with sat'd NaCl solution, dried over MgSO4, filtered and the filtrate was cocentrated give 2.45 g of the title compound which was used without further purification.

Provenance & Evidence