Potassium Carbonate → Tert-butyl 4-(4-iodo-3-methyl-2-oxopyridin-1(2H)-yl)piperidine-1-carboxylate

HRID 2272533Notes

Reaction equation

HRID 2272533 reaction equation
CC1C=CC(S(O[CH:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]2)(=O)=O)=CC=1.[I:25][C:26]1[CH:31]=[CH:30][NH:29][C:28](=[O:32])[C:27]=1[CH3:33].C(=O)([O-])[O-].[K+].[K+]>COCCOCCOC>[I:25][C:26]1[CH:31]=[CH:30][N:29]([CH:12]2[CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19])[CH2:16][CH2:17]2)[C:28](=[O:32])[C:27]=1[CH3:33]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 157347131-(tert-Butoxycarbonyl)-4-(p-toluenesulfonyloxy)piperidineHCID 672620434-iodo-3-methylpyridin-2(1H)-one

Product 1

HCID 118037690Tert-butyl 4-(4-iodo-3-methyl-2-oxopyridin-1(2H)-yl)piperidine-1-carboxylateYield 80.7%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

Tert-butyl 4-(((4-methylphenyl)sulfonyl)oxy)piperidine-1-carboxylate (21.7 g) was added to a mixture of 4-iodo-3-methylpyridin-2(1H)-one (8.98 g) and potassium carbonate (21.1 g) in 1-methoxy-2-(2-methoxyethoxyl)ethane (160 mL) at room temperature. The mixture was stirred at 100 C under nitrogen atmosphere for 22 hours. The mixture was quenched with water at room temperature and extracted with ethyl acetate. The organic layer was separated, washed with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. Toluene was added to the residue. The mixture was concentrated in vacuo. The residue was purified by a silica gel column chromatography (hexane/ethyl acetate) to give the title compound (12.9 g).

Workup

  1. customThe mixture was quenched with water at room temperature
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. additionToluene was added to the residue
  8. concentrationThe mixture was concentrated in vacuo
  9. customThe residue was purified by a silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-3f85687c256249109dd62192f6487a1b
Source dataset
uspto-grants-2015_09
Patent number
US09120777B2

Reaction notes

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