1-Bromo-4-fluorobenzene → 1-Boc-3-(4'-fluorophenyl)-piperidin-4-one

HRID 1437626Notes

Reaction equation

HRID 1437626 reaction equation
CC(C)([O-])C.[Na+].[F:7][C:8]1[CH:13]=[CH:12][C:11](Br)=[CH:10][CH:9]=1.[O:15]=[C:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[F:7][C:8]1[CH:13]=[CH:12][C:11]([CH:21]2[C:16](=[O:15])[CH2:17][CH2:18][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:20]2)=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 99931-Bromo-4-fluorobenzeneHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 23676156Sodium t-butoxide

Product 1

HCID 230801161-Boc-3-(4'-fluorophenyl)-piperidin-4-oneYield 12.4%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

(±)-BINAP (0.90 g), sodium tert-butoxide (5.02 g), tris(dibenzylideneacetone)dipalladium(0) (0.55 g) and toluene (200 ml) were mixed under nitrogen atmosphere, and 4-fluorobromobenzene (10.54 g), and then tert-butyl 4-oxo-1-piperidmecarboxylate (8.0 g) were added thereto. The mixture was stirred at room temperature for 5 minutes, and then at 60° C. for 7 hours (under nitrogen atmosphere). After cooling to room temperature, the reaction solution was washed with water and saturated brine, dried, and then the solvent was evaporated under reduced pressure. The obtained residue was isolated and purified by silica gel column chromatography (ethyl acetate:hexane=1:4) to obtain tert-butyl 3-(4-fluorophenyl)-4-oxo-1-piperidinecarboxylate (1.46 g) as colorless crystals.

Workup

  1. waitat 60° C. for 7 hours (under nitrogen atmosphere)
  2. temperatureAfter cooling to room temperature
  3. washthe reaction solution was washed with water and saturated brine
  4. customdried
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was isolated
  7. custompurified by silica gel column chromatography (ethyl acetate:hexane=1:4)

Sources & evidence

ORD record
ord-89907bfdf915403ab0a2a033f73c818a
Source dataset
uspto-grants-2009_11
Patent number
US07622487B2

Reaction notes

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