Triacetoxyperiodinane → tert-butyl N-methyl-N-(3-oxopropyl)carbamate

Participants

Reaction Steps

Commercially available tert-butyl(3-hydroxypropyl)(methyl)carbamate (1.858 g, 9.82 mmol) was solubilised in DCM (40 ml) and treated with sodium bicarbonate (4.12 g, 49.1 mmol) followed by Dess-Martin reagent (5.21 g, 12.28 mmol). The reaction mixture was stirred at RT for 2 hrs and then partitioned between DCM and sodium bicarbonate solution. Sodium thiosulphate was added and the organic portion was separated. The aqueous layer was extracted with DCM (×2) and the combined organic extracts were dried over MgSO4 (anh), filtered and evaporated under reduced pressure to afford the title compound without further purification;

Provenance & Evidence