m-Chloroperbenzoic acid → rac-(3aR,5S,6aS)-2-[4-(trifluoromethoxy)phenyl]hexahydro-1H-spiro[cyclopenta[c]pyrrole-5,2'-oxiran]-1-one

HRID 1887499Notes

Reaction equation

HRID 1887499 reaction equation
[CH2:1]=[C:2]1[CH2:21][CH:5]2[C:6](=[O:20])[N:7]([C:9]3[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:18])[F:17])=[CH:11][CH:10]=3)[CH2:8][CH:4]2[CH2:3]1.C1C=C(Cl)C=C(C(OO)=[O:30])C=1.C([O-])(O)=O.[Na+]>ClCCl>[F:18][C:16]([F:17])([F:19])[O:15][C:12]1[CH:11]=[CH:10][C:9]([N:7]2[CH2:8][CH:4]3[CH2:3][C:2]4([CH2:21][CH:5]3[C:6]2=[O:20])[CH2:1][O:30]4)=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 866739185-Methylene-2-(4-trifluoromethoxy-phenyl)-hexahydro-cyclopenta[c]pyrrol-1-one

Product 1

HCID 86673919rac-(3aR,5S,6aS)-2-[4-(trifluoromethoxy)phenyl]hexahydro-1H-spiro[cyclopenta[c]pyrrole-5,2'-oxiran]-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-Methylene-2-(4-trifluoromethoxy-phenyl)-hexahydro-cyclopenta[c]pyrrol-1-one (0.78 g, 2.6 mmol) in dichloromethane (20 mL) was added mCPBA (0.9 g, 5.2 mmol) at 0° C., and the mixture was stirred for 6 h at room temperature. Saturated solution of NaHCO3 (30 mL) was added and stirred for another 0.5 h. The mixture was extracted with dichloromethane (2×30 mL), washed with brine (60 mL) and dried over Na2SO4. The solvent was removed and the residue was purified by prep-TLC with petroleum ether/ethyl acetate (1:1) to yield rac-(3aR,5S,6aS)-2-[4-(trifluoromethoxy)phenyl]hexahydro-1H-spiro[cyclopenta[c]pyrrole-5,2′-oxiran]-1-one

Workup

  1. stirringstirred for another 0.5 h
  2. extractionThe mixture was extracted with dichloromethane (2×30 mL)
  3. washwashed with brine (60 mL)
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed
  6. customthe residue was purified by prep-TLC with petroleum ether/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-84fa2e98cc87480f838fc451caf36cdf
Source dataset
uspto-grants-2013_08
Patent number
US08501768B2

Reaction notes

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