Sodium Chloride → HCID 15023847, compound

HRID 1648650Notes

Reaction equation

HRID 1648650 reaction equation
[H-].[Na+].[F:3][C:4]([F:8])([F:7])[CH2:5][OH:6].[C:9]([O:13][C:14]([N:16]1[CH2:20][CH:19]2[O:21][CH:18]2[CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10].[Cl-].[Na+].[CH3:24][S:25](Cl)(=[O:27])=[O:26]>O>[C:9]([O:13][C:14]([N:16]1[CH2:20][CH:19]([O:21][S:25]([CH3:24])(=[O:27])=[O:26])[CH:18]([O:6][CH2:5][C:4]([F:8])([F:7])[F:3])[CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10]

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 64092,2,2-TrifluoroethanolHCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 10103880tert-Butyl 6-Oxa-3-azabicyclo(3.1.0)hexane-3-carboxylate

Product 1

HCID 15023847HCID 15023847, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

1.08 g (0.027 mole) of a 60% w/w dispersion of sodium hydride in mineral oil was added, whilst cooling with water, to 15 ml of 2,2,2-trifluoroethanol, and the mixture was stirred for 20 minutes. At the end of this time, 5.0 g (0.027 mole) of 1-t-butoxycarbonyl-3,4-epoxypyrrolidine were added to the mixture, which was then heated under reflux for 3 hours. The reaction mixture was then mixed with a saturated aqueous solution of sodium chloride and extracted with ethyl acetate. The organic extract was dried over anhydrous sodium sulfate and concentrated by evaporation under reduced pressure. The concentrate was dissolved in 50 ml of pyridine, and 3.23 g (0.028 mole) of methanesulfonyl chloride were added, whilst ice-cooling, to the resulting solution. The mixture was then stirred at room temperature for 5 hours and then allowed to stand overnight at room temperature. After it had been diluted with 300 ml of water, the reaction mixture was extracted with toluene. The organic extract was dried over anhydrous sodium sulfate and concentrated by evaporation under reduced pressure. The residue was purified by column chromatography through silica gel using a 9:1 by volume mixture of toluene and ethyl acetate as the eluent, to afford 7.07 g of 1-t-butoxycarbonyl-3-(2,2,2-trifluoroethoxy)-4-methylsulfonyloxypyrrolidine.

Workup

  1. temperaturewas then heated
  2. temperatureunder reflux for 3 hours
  3. extractionextracted with ethyl acetate
  4. extractionThe organic extract
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. concentrationconcentrated by evaporation under reduced pressure
  7. dissolutionThe concentrate was dissolved in 50 ml of pyridine
  8. temperaturecooling, to the resulting solution
  9. stirringThe mixture was then stirred at room temperature for 5 hours
  10. waitto stand overnight at room temperature
  11. extractionthe reaction mixture was extracted with toluene
  12. extractionThe organic extract
  13. dry with materialwas dried over anhydrous sodium sulfate
  14. concentrationconcentrated by evaporation under reduced pressure
  15. customThe residue was purified by column chromatography through silica gel using a 9:1
  16. additionby volume mixture of toluene and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-3c73bc4830764672bfbee228bdfa25e6
Source dataset
uspto-grants-1995_07
Patent number
US05436367

Reaction notes

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