Methyl morpholine oxide → 1-(Benzo[d][1,3]dioxol-5-ylmethyl)pyrrolidin-3-one

Participants

Reaction Steps

A solution of alcohol 273 (0.78 g, 3.53 mmol) in dry DCM (40 mL) was treated with 4 Å molecular sieves (powder, 3.49 g) and 4-methylmorpholine N-oxide (NMO) (2.11 g, 18.03 mmol) and the suspension was stirred under nitrogen atmosphere for 18 h. The reaction mixture was cooled to 0° C. for the addition of solid tetrapropylammonium perruthenate (TPAP) (0.11 g, 0.31 mmol) and stirred for 30 min, then diluted with DCM, filtered through a Celite® pad, washed with saturated NaHCO3, dried over MgSO4, filtered through a pad of SiO2 (eluent: 5% MeOH in DCM) and concentrated to provide title compound 274 (0.65 g, 84% yield).

Provenance & Evidence