2-Chlorobenzene-1-carboperoxoic acid → tert-Butyl 7-Oxa-3-azabicyclo(4.1.0)heptane-3-carboxylate

HRID 1432522Notes

Reaction equation

HRID 1432522 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]=[CH:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].ClC1C(C(OO)=[O:22])=CC=CC=1>C(Cl)Cl>[C:1]([N:8]1[CH2:13][CH2:12][CH:11]2[O:22][CH:10]2[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 125873982-Chlorobenzene-1-carboperoxoic acidHCID 13094787tert-Butyl 3,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 21991116tert-Butyl 7-Oxa-3-azabicyclo(4.1.0)heptane-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3.29 g of N-BOC-1,2,5,6-tetrahydropyridine in 25 ml of CH2Cl2, a suspension of 6.2 g of chloroperbenzoic acid in 50 ml of CH2Cl2 are added and the mixture obtained is stirred for ca. 12 hours at RT. The mixture obtained is extracted with saturated aqueous NaHCO3-solution and 0.5 m aqueous Na2S5O3-solution and the organic phase obtained is washed, dried and the solvent is evaporated. N-BOC-3,4-epoxy-piperidine is obtained.

Workup

  1. additionare added
  2. customthe mixture obtained
  3. customThe mixture obtained
  4. extractionis extracted with saturated aqueous NaHCO3-solution and 0.5 m aqueous Na2S5O3-solution
  5. customthe organic phase obtained
  6. washis washed
  7. customdried
  8. customthe solvent is evaporated

Sources & evidence

ORD record
ord-572c544fac55488ca52dfdd0c8ea06ea
Source dataset
uspto-grants-2009_11
Patent number
US07612103B2

Reaction notes

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