tert-Butyl 5-(hydroxymethyl)pyridin-2-ylcarbamate → tert-butyl N-(5-formylpyridin-2-yl)carbamate

Participants

Reaction Steps

5 (5-hydroxymethyl-pyridin-2-yl)-carbamic acid tert-butyl ester (7.00 g, 31.2 mmol) was dissolved in dry DMSO (50 mL) and the reaction flask immersed in a waterbath at 15° C. TEA (13.1 ml, 94.0 mmol) was added, followed by sulfur trioxide pyridine complex (15.0 g, 94.0 mmol) in portions. The reaction mixture was stirred for further 45 min and poured onto crushed ice. The product was extracted with diethyl ether and the combined organic extracts were washed with brine, dried and concentrated under reduced pressure. Recrystallisation from hexane/CH2Cl2 afforded (5-formyl-pyridin-2-yl)-carbamic acid tert-butyl ester (5.40 g, 78%) as white crystals.

Provenance & Evidence