Ethylene Glycol → 2-(2-fluoro-4-nitrophenyl)-hexahydro-1H-spiro[cyclopenta[c]pyrrol-5,2'-[1,3]dioxolane]

HRID 1891398Notes

Reaction equation

HRID 1891398 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]1[CH2:15][CH:14]2[CH2:16][C:17](=[O:19])[CH2:18][CH:13]2[CH2:12]1.[CH2:20](O)[CH2:21][OH:22].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]1[CH2:15][CH:14]2[CH2:16][C:17]3([CH2:18][CH:13]2[CH2:12]1)[O:22][CH2:21][CH2:20][O:19]3

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 521998p-Toluenesulfonic acid monohydrateHCID 711829272-(2-Fluoro-4-nitrophenyl)-5-oxo-hexahydro-cyclopenta[c]pyrrol

Product 1

HCID 711829442-(2-fluoro-4-nitrophenyl)-hexahydro-1H-spiro[cyclopenta[c]pyrrol-5,2'-[1,3]dioxolane]

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

19.74 g (74.7 mmol) of 2-(2-fluoro-4-nitrophenyl)-5-oxo-hexahydro-cyclopenta[c]pyrrol prepared in the step 3 and 5.0 ml (89.6 mmol) of ethylene glycol were dissolved in 200 ml of benzene, 1.00 g (5.2 mmol) of p-toluene sulfonic acid hydrate was added, and the mixture was heated to reflux for 1 hour while removing generated water. After the reaction was completed, the mixture was washed with a saturated aqueous solution of sodium carbonate and water, and then, the organic layer was dried over magnesium sulfate, filtered and concentrated under reduced pressure to obtain the title compound, of which NMR data is as follow.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 1 hour
  3. customwhile removing
  4. washthe mixture was washed with a saturated aqueous solution of sodium carbonate and water
  5. dry with materialthe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c0e85634b9594580ae8953478809e123
Source dataset
uspto-grants-2013_08
Patent number
US08507540B2

Reaction notes

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