tert-butyl N-(1-hydroxy-2-methylpropan-2-yl)carbamate → tert-butyl N-(2-methyl-1-oxopropan-2-yl)carbamate

Participants

Reaction Steps

To a solution 2-(tert-Butoxycarbonylamino)-2-methyl-1-propanol (5.7 g, 30.0 mmol) in triethylamine (42 mL) was added a mixture of sulfur trioxide pyridine complex (14.3 g, 90.0 mmol) in anhydrous DMSO (dimethylsulfoxide) (50 mL) at room temperature. The reaction was stirred for 1 hour under nitrogen and concentrated. The residue was dissolved in EtOAc (200 mL), washed with water (100 mL) and brine (100 mL), dried over sodium sulfate, and concentrated to give crude 2-(tert-butoxycarbonylamino)-2-methyl propionaldehyde as yellow oil. Purification by distillation afforded 4.90 g (87%) of waxy, white solid: 1H NMR (CDCl3) δ 1.30 (s, 6H), 1.41 (s, 9H), 4.97 (br, 1 H), 9.40 (s, 1H).

Provenance & Evidence