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

HRID 2171807Notes

Reaction equation

HRID 2171807 reaction equation
OO.F[C:4](F)(F)[C:5]([O:7][C:8](=O)[C:9](F)(F)F)=O.[CH2:16]([N:23]1CC=C(C)[CH2:25][CH2:24]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[O-]S([O-])=O.[Na+].[Na+]>C(Cl)Cl>[CH2:16]([N:23]1[CH2:24][CH2:25][C:8]2([CH3:9])[CH:5]([O:7]2)[CH2:4]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 9845Trifluoroacetic anhydrideHCID 24437Sodium SulfiteHCID 64215721-Benzyl-4-methyl-1,2,3,6-tetrahydropyridine

Product 1

HCID 121434103-Benzyl-6-methyl-7-oxa-3-azabicyclo[4.1.0]heptane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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).

Workup

  1. stirringstirring at 50° C. for additional 3 hours
  2. extractionextracting with DCM
  3. washThe organic layer was washed with saturated aqueous sodium bicarbonate
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column (chloroform/MeOH)

Sources & evidence

ORD record
ord-f12c256768294fb89b9096fd1caeafd5
Source dataset
uspto-grants-2015_06
Patent number
US09051339B2

Reaction notes

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