Dimethyl Sulfoxide → 1-Boc-4-formyl-azepane

Participants

Reaction Steps

At −60° C., a solution of DMSO (1.73 ml, 24.4 mmol) in CH2Cl2 (20 mL) was added dropwise to a 2M solution of oxalyl chloride (1.28 mL, 14.7 mmol) in CH2Cl2 (7 mL). The mixture was stirred for 20 minutes and then a solution of tert-butyl 4-(hydroxymethyl)azepane-1-carboxylate (2.8 g, 12.2 mmol) in CH2Cl2 (7 mL) was added dropwise. The mixture was stirred for 10 minutes and triethylamine (8.51 ml, 61.1 mmol) was slowly added. The reaction mixture was warmed to ambient temperature and water was added. When the mixture became clear, it was extracted with CH2Cl2, the solvent evaporated to afford crude tert-butyl 4-formylazepane-1-carboxylate (2.78 g, 100%).

Provenance & Evidence