Hydrogen Peroxide → 3-Benzyl-6-methyl-7-oxa-3-azabicyclo[4.1.0]heptane

Participants

Reaction Steps

To a mixture of a 30% hydrogen peroxide solution (3.6 mL) and DCM (120 mL) were added trifluoroacetic anhydride (6.0 mL) at 0° C., and a solution of 1-benzyl-4-methyl-1,2,3,6-tetrahydropyridine (2.9 g) in DCM (10 mL) was further added thereto, followed by stirring at room temperature for 12 hours and then stirring at 50° C. for additional 3 hours. To the reaction mixture was added an aqueous Na2SO3 solution, followed by stirring until peroxides disappeared, and then extracting with DCM. The organic layer was washed with saturated aqueous sodium bicarbonate, dried over MgSO4, and then concentrated under reduced pressure. The residue was purified by silica gel column (chloroform/MeOH) to obtain 3-benzyl-6-methyl-7-oxa-3-azabicyclo[4.1.0]heptane (1.8 g).

Provenance & Evidence