(2R,5R)-2-(t-butyl)-5-((1R)-3-oxocyclopentyl)-5-phenyl-1,3-dioxolan-4-one → (2R,5R)-2-(t-butyl)-5-((1R)-3,3-difluorocyclopentyl)-5-phenyl-1,3-dioxolan-4-One

HRID 1785256Notes

Reaction equation

HRID 1785256 reaction equation
[C:1]([C@H:5]1[O:9][C:8](=[O:10])[C@@:7]([C@@H:17]2[CH2:21]CC(=O)[CH2:18]2)([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[O:6]1)([CH3:4])([CH3:3])[CH3:2].F[C:24]([F:35])([F:34])[CH2:25]N(OS(=O)(=O)O)CC>C(Cl)(Cl)Cl>[C:1]([C@H:5]1[O:9][C:8](=[O:10])[C@@:7]([C@@H:17]2[CH2:21][CH2:25][C:24]([F:34])([F:35])[CH2:18]2)([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[O:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 11174148(2R,5R)-2-(t-butyl)-5-((1R)-3-oxocyclopentyl)-5-phenyl-1,3-dioxolan-4-oneHCID 131724719Trifluorodiethylaminosulfuric acid

Product 1

HCID 10592061(2R,5R)-2-(t-butyl)-5-((1R)-3,3-difluorocyclopentyl)-5-phenyl-1,3-dioxolan-4-One

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 2.8 g of (2R, 5R)-2-(t-butyl)-5-((1R)-3-oxocyclopentyl)-5-phenyl-1,3-dioxolan-4-one in 30 ml of chloroform, 4.89 ml of trifluorodiethylaminosulfuric acid was added under cooling with ice, followed by 20 hours' stirring at room temperature. The reaction liquid was diluted with chloroform, washed successively with water and with saturated brine, and dried over anhydrous magnesium sulfate. Distilling the solvent off under reduced pressure, the resulting residue was purified on silica gel column chromatography (eluent: hexane/ethyl acetate=20/1) to provide 2.4 g of the title compound.

Workup

  1. temperatureunder cooling with ice
  2. customThe reaction liquid
  3. washwashed successively with water and with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationDistilling the solvent off under reduced pressure
  6. customthe resulting residue was purified on silica gel column chromatography (eluent: hexane/ethyl acetate=20/1)

Sources & evidence

ORD record
ord-c589c582224e448c9b111b78989fe13c
Source dataset
uspto-grants-2009_03
Patent number
US07504432B2

Reaction notes

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