Water → Benzyl 4-(5-methyl-2-oxo-1,2-dihydropyridin-4-yloxy)piperidine-1-carboxylate

HRID 1895719Notes

Reaction equation

HRID 1895719 reaction equation
[OH:1][C:2]1[C:7]([CH3:8])=[CH:6][NH:5][C:4](=[O:9])[CH:3]=1.CS(O[CH:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])[CH2:17][CH2:16]1)(=O)=O.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C.CCOC(C)=O>[CH3:8][C:7]1[C:2]([O:1][CH:15]2[CH2:20][CH2:19][N:18]([C:21]([O:23][CH2:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)=[O:22])[CH2:17][CH2:16]2)=[CH:3][C:4](=[O:9])[NH:5][CH:6]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 547201464-hydroxy-5-methylpyridin-2(1H)-oneHCID 58303455Benzyl 4-((methanesulfonyl)oxy)piperidine-1-carboxylate

Product 1

HCID 67367290Benzyl 4-(5-methyl-2-oxo-1,2-dihydropyridin-4-yloxy)piperidine-1-carboxylateYield 95.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Hydroxy-5-methylpyridin-2(1H)-one (554 mg, 4.43 mmol), benzyl 4-(methylsulfonyloxy)piperidine-1-carboxylate (2081 mg, 6.64 mmol), and potassium carbonate (1224 mg, 8.86 mmol) were stirred in DMF (12 mL) at 100° C. under nitrogen for 14 hours. 100 mL water and 100 mL EtOAc was added and then washed the EtOAc layer with 2×100 mL additional water. The organic layer was dried with Na2SO4, filtered, and concentrated to give 1454 mg of a brown oil. The oil was purified by flash chromatography (0-5% MeOH/CH2Cl2) to give product (280 mg, 0.82 mmol, 18%) as a pale tan foam. MS (ESI) 343.4 (M+1).

Workup

  1. washwashed the EtOAc layer with 2×100 mL additional water
  2. dry with materialThe organic layer was dried with Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d7d0061aa0094e1d8f55916ee53ab2e6
Source dataset
uspto-grants-2013_08
Patent number
US08513424B2

Reaction notes

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