Hydrochloric Acid → 3-(4,4-difluoro-3-methylene-3,4-dihydro-2H-pyrrol-5-yl)-2-(trifluoromethyl)pyridine

HRID 1426693Notes

Reaction equation

HRID 1426693 reaction equation
[F:1][C:2]([F:26])([C:14](=O)[C:15]1[C:16]([C:21]([F:24])([F:23])[F:22])=[N:17][CH:18]=[CH:19][CH:20]=1)[C:3](=[CH2:13])[CH2:4][NH:5]C(=O)OC(C)(C)C.Cl>C(O)(=O)C>[F:1][C:2]1([F:26])[C:14]([C:15]2[C:16]([C:21]([F:24])([F:23])[F:22])=[N:17][CH:18]=[CH:19][CH:20]=2)=[N:5][CH2:4][C:3]1=[CH2:13]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59826893HCID 59826893, compound

Product 1

HCID 598268813-(4,4-difluoro-3-methylene-3,4-dihydro-2H-pyrrol-5-yl)-2-(trifluoromethyl)pyridineYield 83%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of tert-butyl {3,3-difluoro-2-methylene-4-oxo-4-[2-(trifluoromethyl)pyridin-3-yl]butyl}carbamate (3.25 g) in acetic acid (10 mL) was added dropwise concentrated hydrochloric acid (3 mL). The obtained mixture was stirred at room temperature for 2 hr, and concentrated under reduced pressure. Saturated aqueous sodium hydrogen carbonate solution was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed successively with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane:ethyl acetate=3:1) to give the title compound as a yellow oil (yield 1.85 g, 83%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionSaturated aqueous sodium hydrogen carbonate solution was added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed successively with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent: hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-9949bf2518124358ba8426c940446693
Source dataset
uspto-grants-2015_01
Patent number
US08933105B2

Reaction notes

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