Ethyl bromopyruvate → 4-(4-Ethoxycarbonyl-thiazol-2-yl)-4-methyl-piperidine-1-carboxylic acid tert-butyl ester

HRID 871902Notes

Reaction equation

HRID 871902 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH3:17])([C:14](=[S:16])[NH2:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:19][C:20](=O)[C:21]([O:23][CH2:24][CH3:25])=[O:22]>CCO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:14]2[S:16][CH:19]=[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[N:15]=2)([CH3:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 57473378HCID 57473378, compound

Product 1

HCID 579868564-(4-Ethoxycarbonyl-thiazol-2-yl)-4-methyl-piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-methyl-4-thiocarbamoyl-piperidine-1-carboxylic acid tert-butyl ester (1 g, 4 mmol) in EtOH (10 mL) was added ethyl bromopyruvate (0.78 g, 4 mmol) at room temperature. The mixture was heated to refluxing for 3 hours. After cooling to room temperature, the solvent was removed in vacuo. The residue was dissolved in methylene chloride (15 mL), Et3N (1 mL) and di-tert-butyl dicarbonate (1.3 g) were added to the solution. The mixture was stirred at room temperature overnight. The mixture was washed with H2O and brine. After drying (Na2SO4), the solvent was removed in vacuo, and the residue was purified by silica column chromatography with EtOAc/hexanes to afford the desired product.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto refluxing for 3 hours
  3. customthe solvent was removed in vacuo
  4. dissolutionThe residue was dissolved in methylene chloride (15 mL)
  5. additionEt3N (1 mL) and di-tert-butyl dicarbonate (1.3 g) were added to the solution
  6. washThe mixture was washed with H2O and brine
  7. dry with materialAfter drying (Na2SO4)
  8. customthe solvent was removed in vacuo
  9. customthe residue was purified by silica column chromatography with EtOAc/hexanes

Sources & evidence

ORD record
ord-82d8202c63874ac4a105c6f2e5891940
Source dataset
uspto-grants-2015_03
Patent number
US08975258B2

Reaction notes

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