Methyl morpholine oxide → Benzyl 3,3-dimethyl-4-oxopyrrolidine-1-carboxylate

Participants

Reaction Steps

A suspension of benzyl 4-hydroxy-3,3-dimethylpyrrolidine-1-carboxylate (4.07 g, 16.3 mmol) in acetonitrile (50 mL), was added 4-methylmorpholine-4-oxide (3.82 g, 32.7 mmol) and tetrapropylammonium perruthenate (0.42 mL, 1.63 mmol). The mixture was stirred at rt for 18 h. The reaction was concentrated and purified using silica gel chromatography, eluting with 0-30% ethyl acetate in hexanes. Benzyl 3,3-dimethyl-4-oxopyrrolidine-1-carboxylate (2.92 g, 68% yield) was obtained as a colorless oil. 1H NMR (400 MHz, CHLOROFORM-d) δ 7.49-7.31 (m, 5H), 5.19 (s, 2H), 3.93 (br. s., 2H), 3.61 (s, 2H), 1.17 (s, 6H); MS (ES+) m/z: 248.1 (M+H); LC retention time: 3.24 min (analytical HPLC Method I).

Provenance & Evidence