Water → HCID 58293355, compound

HRID 1912415Notes

Reaction equation

HRID 1912415 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]([OH:16])=[O:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[C:24]([F:28])([F:27])[CH:25]=[CH2:26].O>CN(C)C=O>[F:27][C:24]([F:28])=[CH:25][CH2:26][O:15][C:14]([CH:10]1[CH2:11][CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9]1)=[O:16]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 5550853-bromo-3,3-difluoroprop-1-eneHCID 27356471-((Tert-butoxy)carbonyl)piperidine-3-carboxylic acid

Product 1

HCID 58293355HCID 58293355, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of piperidine-1,3-dicarboxylic acid 1-tert-butyl ester (30.0 g) in N,N-dimethylformamide (300 ml) were added potassium carbonate (36.2 g) and 3-bromo-3,3-difluoropropene (16 ml), and the mixture was stirred at 60° C. for 4.5 hours. To the reaction mixture was added water, and the mixture was extracted with n-hexane/ethyl acetate (1/1) solution. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=10/1) to give the titled compound (33.5 g).

Workup

  1. extractionthe mixture was extracted with n-hexane/ethyl acetate (1/1) solution
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-55dfd369925c46a19f6aaab4a98f7f70
Source dataset
uspto-grants-2013_12
Patent number
US08609647B2

Reaction notes

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