Potassium Carbonate → Tert-butyl 4-(2-oxo-1,2-dihydropyridin-4-yloxy)piperidine-1-carboxylate

HRID 1676175Notes

Reaction equation

HRID 1676175 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][NH:5][C:4](=[O:8])[CH:3]=1.CS(O[CH:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CCOC(C)=O.O>[O:8]=[C:4]1[CH:3]=[C:2]([O:1][CH:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]2)[CH:7]=[CH:6][NH:5]1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidineHCID 546960044-Hydroxy-2(1H)-pyridinone

Product 1

HCID 67366878Tert-butyl 4-(2-oxo-1,2-dihydropyridin-4-yloxy)piperidine-1-carboxylateYield 38.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

A stirring mixture of 4-hydroxypyridin-2(1H)-one (1.2 g, 10.8 mmol, prepared according to the procedure described at Step A of Example 8), tert-butyl 4-(methylsulfonyloxy)piperidine-1-carboxylate (4.83 g, 17.3 mmol, prepared according to the procedure described at Step C of Example 1) and potassium carbonate (3.13 g, 22.7 mmol) in DMF (45 mL) was heated at 90° C. for 14 brs and then cooled to room temperature. The resulting mixture was diluted with EtOAc and H2O and the aqueous layer was extracted further with EtOAc (5×). The combined extracts were washed with brine, dried (Na2SO4) and evaporated under reduced pressure. The residual was purified by flash chromatography on silica gel (0 to 10% MeOH/CH2Cl2) to yield 1.23 g (38.7%) of the product as a pinkish solid. MS (ESI) 295 (M+H).

Workup

  1. customprepared
  2. customprepared
  3. temperaturecooled to room temperature
  4. extractionthe aqueous layer was extracted further with EtOAc (5×)
  5. washThe combined extracts were washed with brine
  6. dry with materialdried (Na2SO4)
  7. customevaporated under reduced pressure
  8. customThe residual was purified by flash chromatography on silica gel (0 to 10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-26db20b5b6864f8090ae70a58c33bbb1
Source dataset
uspto-grants-2011_08
Patent number
US08003796B2

Reaction notes

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