tert-Butyl hydroperoxide → HCID 71279181, compound

HRID 1621173Notes

Reaction equation

HRID 1621173 reaction equation
[O:1]=[C:2]([C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1)[CH2:3][C:4]([O:6][CH3:7])=[O:5].[CH2:14]([NH2:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(OO)(C)(C)C.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(OCC)(=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:15]1([C:14]2[O:1][C:2]([C:8]3[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=3)=[C:3]([C:4]([O:6][CH3:7])=[O:5])[N:21]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 6410tert-Butyl hydroperoxideHCID 7504BenzylamineHCID 24477Sodium ThiosulfateHCID 1086453-Pyridinepropanoic acid, beta-oxo-, methyl ester

Product 1

HCID 71279181HCID 71279181, compoundYield 178.9%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of methyl 3-oxo-3-(pyridin-3-yl)propanoate (4 g, 22.3 mmol) in ethyl acetate (200 mL) were added at RT tetrabutylammonium iodide (1.65 g, 4.46 mmol), benzylamine (4.78 g, 4.87 mL, 44.6 mmol) and tert-butyl hydroperoxide (5.5M solution in decane, 16.2 mL, 89.3 mmol). The reaction mixture was stirred at 40° C. for 19 h. Sodium thiosulphate (10% aqueous solution, 200 mL) was added at RT and the reaction mixture was stirred for 10 min (until negative peroxide test). The aqueous phase was separated, the organic phase was washed with water (2×100 mL) and brine (20 mL). The aqueous phases were back-extracted with ethyl acetate (1×100 mL) and the combined organic phase was dried over MgSO4, filtered and evaporated to give 11.18 g of yellow semi-solid. The product was obtained after purification by flash chromatography (using silica gel and an ethyl acetate/heptane gradient) as yellow solid (1.33 g, 4.75 mmol, 21.3% yield).

Workup

  1. customThe aqueous phase was separated
  2. washthe organic phase was washed with water (2×100 mL) and brine (20 mL)
  3. extractionThe aqueous phases were back-extracted with ethyl acetate (1×100 mL)
  4. dry with materialthe combined organic phase was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-58ce5dfd33314de7b1820fb6261f80a2
Source dataset
uspto-grants-2014_07
Patent number
US08772510B2

Reaction notes

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