Triacetoxyperiodinane → benzyl N-(1,1-dimethyl-3-oxo-propyl)carbamate

Participants

Reaction Conditions

Reaction Steps

To a 100-mL round-bottomed flask was added benzyl(4-hydroxy-2-methylbutan-2-yl)carbamate (1.60 g, 6.74 mmol) and dess-martinperiodinane (24.72 mL, 7.42 mmol) (0.3 M in DCM, Sigma-Aldrich) at 0° C. The reaction was stirred at 0° C. for 40 min, then diluted with DCM (100 mL). The mixture was washed with sat. NaHCO3, and brine. The organic layer was dried (MgSO4), filtered and concentrated. The residue was purified via silica gel chromatography (eluted with 10-60% EtOAc in Hex) to give benzyl(2-methyl-4-oxobutan-2-yl)carbamate (1.04 g, 4.42 mmol, 65% yield) as a colorless oil. MS (ESI, pos. ion) m/z: 236.1 (M+1).

Provenance & Evidence