Pyridine → Tert-butyl 2-carbamoyl-4,4-difluoropiperidine-1-carboxylate

HRID 74901

Reaction equation

HRID 74901 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([F:15])([F:14])[CH2:10][CH:9]1[C:16]([OH:18])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N:19]1C=CC=CC=1.C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O.C(=O)(O)[O-].[NH4+]>O1CCOCC1>[C:16]([CH:9]1[CH2:10][C:11]([F:15])([F:14])[CH2:12][CH2:13][N:8]1[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])(=[O:18])[NH2:19]

Participants

6

Reactant 4

HCID 1049PyridineHCID 14013Ammonium BicarbonateHCID 90495Di-tert-butyl dicarbonateHCID 101069001-((Tert-butoxy)carbonyl)-4,4-difluoropiperidine-2-carboxylic acid2×

Product 1

HCID 67286514Tert-butyl 2-carbamoyl-4,4-difluoropiperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 1-tert-butoxycarbonyl-4,4-difluoro-piperidine-2-carboxylic acid, 13f, (1.67 g, 6.30 mmol) in 1,4-dioxane (12 mL) was added pyridine (0.35 mL, 4.33 mmol), followed by di-tert-butyl dicarbonate (1.78 g, 8.17 mmol) and ammonium bicarbonate (0.63 g, 7.86 mmol). The reaction mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure and the residue was taken up in EtOAc. The organic phase was washed with water, aqueous saturated KHSO4 solution, brine, dried over Na2SO4, filtered and evaporated to dryness. The crude residue was used without further purification.

Workup

  1. customThe solvent was removed under reduced pressure
  2. washThe organic phase was washed with water, aqueous saturated KHSO4 solution, brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe crude residue was used without further purification

Sources & evidence

ORD record
ord-e7fe087c2d5d46bab2cfd714b40831b4
Source dataset
uspto-grants-2014_09
Patent number
US08829007B2

Linked notes

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