m-Chloroperbenzoic acid → tert-Butyl 7-Oxa-3-azabicyclo(4.1.0)heptane-3-carboxylate

HRID 82470Notes

Reaction equation

HRID 82470 reaction equation
[C:1]([N:8]1[CH2:13][CH:12]=[CH:11][CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].ClC1C=C(C=CC=1)C(OO)=[O:19]>ClCCl>[CH:12]12[O:19][CH:11]1[CH2:10][CH2:9][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:13]2

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic 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 6344DichloromethaneSolvent

Procedure

To a solution of N-boc-1,2,3,6-tetrahydropyridine (3.63 g, 21.0 mmol) in 40 mL of dichloromethane was added 3-chloroperoxybenzoic acid (2.75 g, 15.0 mmol). The reaction was stirred at room temperature for 4 h, then washed 3× with saturated aqueous potassium carbonate and once with brine. The solution was dried over sodium sulfate, filtered, and concentrated in vacuo to provide crude tert-butyl 7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate that gave a proton NMR spectra consistent with theory.

Workup

  1. washwashed 3× with saturated aqueous potassium carbonate
  2. dry with materialThe solution was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1eef6bacf83b446a937e3dad4ae718d1
Source dataset
uspto-grants-2014_09
Patent number
US08846702B2

Reaction notes

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