Ozone → 2-(4-Trifluoromethoxy-phenyl)-hexahydro-cyclopenta[c]pyrrole-1,5-dione

HRID 1887497Notes

Reaction equation

HRID 1887497 reaction equation
[O:1]=[O+][O-].C=[C:5]1[CH2:24][CH:8]2[C:9](=[O:23])[N:10]([C:12]3[CH:17]=[CH:16][C:15]([O:18][C:19]([F:22])([F:21])[F:20])=[CH:14][CH:13]=3)[CH2:11][CH:7]2[CH2:6]1>C(Cl)Cl>[F:20][C:19]([F:21])([F:22])[O:18][C:15]1[CH:16]=[CH:17][C:12]([N:10]2[CH2:11][CH:7]3[CH2:6][C:5](=[O:1])[CH2:24][CH:8]3[C:9]2=[O:23])=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 24823Ozone2×HCID 866739185-Methylene-2-(4-trifluoromethoxy-phenyl)-hexahydro-cyclopenta[c]pyrrol-1-one

Product 1

HCID 710087992-(4-Trifluoromethoxy-phenyl)-hexahydro-cyclopenta[c]pyrrole-1,5-dioneYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A slow stream of ozone was bubbled into a solution of 5-Methylene-2-(4-trifluoromethoxy-phenyl)-hexahydro-cyclopenta[c]pyrrol-1-one (0.1 g, 0.34 mmol) in 30 mL of methylene chloride at −78° C. The stream of ozone was maintained until a slight blue color persisted. After removal of excess ozone with a stream of nitrogen, 2 mL of dimethyl sulfide was added at −78° C. The mixture was then allowed to warm to room temperature, and stirred for overnight. The solvent was removed, and the crude product was purified by prep-TLC (MeOH: dichloromethane=1:50) to yield the title compound (50 mg, 50%). 1H NMR (300 MHz, CDCl3): δ 7.69-7.65 (m, 2H), 7.26-7.22 (m, 2H), 4.20 (t, 1H, J=8.4 Hz), 3.69-3.66 (m, 1H), 3.45-3.38 (m, 1H), 3.22-3.16 (m, 1H), 2.88-2.56 (m, 3H), 2.25-2.18 (m, 1H); LC-MS: 300.1 [M+1]+.

Workup

  1. customAfter removal of excess ozone with a stream of nitrogen, 2 mL of dimethyl sulfide
  2. additionwas added at −78° C
  3. customThe solvent was removed
  4. customthe crude product was purified by prep-TLC (MeOH: dichloromethane=1:50)

Sources & evidence

ORD record
ord-44806c0607ba4d5db64b3160b1d3507e
Source dataset
uspto-grants-2013_08
Patent number
US08501768B2

Reaction notes

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