Triethylamine → 2-(2-Fluoro-4-nitrophenyl)-5-oxo-hexahydro-cyclopenta[c]pyrrol

HRID 1891397Notes

Reaction equation

HRID 1891397 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][CH:17]([OH:19])[CH2:18][CH:13]2[CH2:12]1.C(N(CC)CC)C>C(Cl)Cl>[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

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 71182928HCID 71182928, compound

Product 1

HCID 711829272-(2-Fluoro-4-nitrophenyl)-5-oxo-hexahydro-cyclopenta[c]pyrrolYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

And, then, the 2-(2-fluoro-4-nitrophenyl)-octahydro-5-hydroxycyclopenta[c]pyrrol (44.4 mmol) prepared in the step 2 was dissolved in 100 ml of methylene chloride and slowly added over 30 minutes, the mixture was stirred for 1 hour while maintaining the temperature, and then, 30.93 ml (221.9 mmol) of triethylamine was slowly added over 20 minutes, the temperature was raised to room temperature, and the mixture was stirred for 2 hours. After the reaction was completed, 100 mL of methylene chloride was added to dilute the mixture, and then, the mixture was washed with water and a saturated aqueous solution of sodium chloride, and the organic layer was dried over magnesium sulfate, filtered and concentrated under reduced pressure. The concentrate was recrystallized under ethanol solvent to obtain 11.1 g (95%) of the title compound.

Workup

  1. additionslowly added over 30 minutes
  2. temperaturewhile maintaining the temperature
  3. stirringthe mixture was stirred for 2 hours
  4. additionto dilute the mixture
  5. washthe mixture was washed with water
  6. dry with materiala saturated aqueous solution of sodium chloride, and the organic layer was dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe concentrate was recrystallized under ethanol solvent

Sources & evidence

ORD record
ord-ed4881d456e44f178aab65d5cada4bf8
Source dataset
uspto-grants-2013_08
Patent number
US08507540B2

Reaction notes

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