m-Chloroperbenzoic acid → Naphthalen-2-ylmethyl 6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate

HRID 1095703Notes

Reaction equation

HRID 1095703 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[N:12]1([C:17]([O:19][CH2:20][C:21]2[CH:30]=[CH:29][C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=2)=[O:18])[CH2:16][CH:15]=[CH:14][CH2:13]1>C(Cl)(Cl)Cl.C([O-])(O)=O.[Na+]>[CH:14]12[O:9][CH:15]1[CH2:16][N:12]([C:17]([O:19][CH2:20][C:21]1[CH:30]=[CH:29][C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=1)=[O:18])[CH2:13]2

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 66781493naphthalen-2-ylmethyl 2,5-dihydro-1H-pyrrole-1-carboxylate

Product 1

HCID 86638608Naphthalen-2-ylmethyl 6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylateYield 43.6%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

mCPBA (4.203 g, 17.04 mmol) was added to a solution of naphthalen-2-ylmethyl 2,5-dihydro-1H-pyrrole-1-carboxylate (2.15 g, 8.52 mmol) in chloroform (35 mL), and the reaction was stirred for 4 days. The reaction mixture was diluted with saturated NaHCO3 and chloroform, and the organic layer was washed with CHCl3, dried over sodium sulfate and condensed. The residue was purified by silica gel chromatography, eluting with a gradient from 1% EtOAc/DCM to 15% EtOAc/DCM, to provide the desired product as a solid (1.0 g).

Workup

  1. washthe organic layer was washed with CHCl3
  2. dry with materialdried over sodium sulfate and condensed
  3. customThe residue was purified by silica gel chromatography
  4. washeluting with a gradient from 1% EtOAc/DCM to 15% EtOAc/DCM

Sources & evidence

ORD record
ord-c23be40b3b55406ba0eb7dfa9802f903
Source dataset
uspto-grants-2012_03
Patent number
US08138181B2

Reaction notes

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