m-Chloroperbenzoic acid → N-Boc-3-pyrroline oxide

Participants

Reaction Steps

To a stirred solution of N-Boc-3-pyrroline (1.69 g, 10 mmol) in CH2Cl2 (20 mL) was added m-chloroperbenzoic acid (MCPBA) (˜85%, 5.2 g) in CH2Cl2 (20 mL) dropwise, and stirring was continued at room temperature overnight. The solution was extracted with saturated aqueous NaHCO3, saturated aqueous Na2SO3 and saturated aqueous NaHCO3 successively. The organic layer was dried over Na2SO4 and filtered. The solvent was evaporated and the residue was purified by flash chromatography (20% ethyl acetate in hexane) to give the product as an oil (1.54 g, 82%): 1H NMR (300 MHz, CDCl3) δ 3.77 (dd, J=22, 13 Hz, 2H), 3.66 (m, 2H), 3.31 (dd, J=13, 3 Hz, 2H), 1.44 (s, 9H).

Provenance & Evidence