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

HRID 2171807노트

반응식

HRID 2171807 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-f12c256768294fb89b9096fd1caeafd5
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09051339B2

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