Dimethyl Sulfide → HCID 22839837, compound

Participants

Reaction Conditions

Reaction Steps

A solution of methyl [(4R)-2-oxo-4-(1,2,4-trioxolan-3-ylmethyl)azetidin-1-yl]glyoxylate (320 mg) and dimethyl sulfide (2 ml) in a mixture of methanol (10 ml) and dichloromethane (9 ml) was stirred at 5° C. for six hours, at room temperature for 15 hours, and at 55° C. for four hours. The resultant solution was concentrated and the residue was dissolved in a mixture of dimethyl sulfide (2 ml) and methanol (15 ml). Silica gel (100 mg) was added and the mixture was stirred at room temperature for four days, at 50° C. for eight hours, and at 60° C. for seven hours. After evaporation of the solvent, the residue was chromatographed on silica gel (7 g) eluting with 2-5% methanol in dichloromethane to give (4R)-4-(2,2-dimethoxyethyl)-2-oxo-azetidine (57 mg) as an impure oil and (4R)-4-(2-oxoethyl)-2-oxoazetidine (31 mg). Further purification of the impure oil on silica gel (4 g) eluting with 0.5-2% methanol in dichloromethane afforded the pure oil (31 mg) of the former compound.

Provenance & Evidence