Formate → 2-(5-Ethyloxazol-2-yl)ethylamine

HRID 601621Notes

Reaction equation

HRID 601621 reaction equation
C([O-])=O.C(OC(=O)[NH:13][CH2:14][CH2:15][C:16]1[O:17][C:18]([CH2:21][CH3:22])=[CH:19][N:20]=1)C1C=CC=CC=1>CO.[Pd]>[CH2:21]([C:18]1[O:17][C:16]([CH2:15][CH2:14][NH2:13])=[N:20][CH:19]=1)[CH3:22]

Participants

5

Reactant 2

HCID 283FormateHCID 57636953Benzyl [2-(5-ethyloxazol-2-yl)ethyl]carbamate

Product 1

HCID 115428012-(5-Ethyloxazol-2-yl)ethylamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Ammnonium formate (0.316 g, 5 mmol) is added to a solution of [2-(5-ethyl-oxazol-2-yl)-ethyl]-carbamic acid benzyl ester (step 3) (1.66 mmol) in methanol (15 ml) and 10% Pd on carbon (125 mg) is added under an inert atmosphere. The mixture is stirred at ambient temperature for 2 hours. The catalyst is removed by filtration and the filtrate is evaporated. The residue is diluted with dichloromethane, filtered to remove undissolved solid and the solvent is removed. The residue is dissolved in DCM and treated with 1M aqueous sodium hydroxide solution (5 ml). The organic extract is separated, dried (MgSO4), filtered and the solvent is removed. Crystallisation from ethyl acetate/dichloromethane affords the titled compound.

Workup

  1. additionis added under an inert atmosphere
  2. customThe catalyst is removed by filtration
  3. customthe filtrate is evaporated
  4. additionThe residue is diluted with dichloromethane
  5. filtrationfiltered
  6. customto remove undissolved solid
  7. customthe solvent is removed
  8. dissolutionThe residue is dissolved in DCM
  9. additiontreated with 1M aqueous sodium hydroxide solution (5 ml)
  10. extractionThe organic extract
  11. customis separated
  12. dry with materialdried (MgSO4)
  13. filtrationfiltered
  14. customthe solvent is removed
  15. customCrystallisation from ethyl acetate/dichloromethane

Sources & evidence

ORD record
ord-85fabe98a36d485ab1df99a083387309
Source dataset
uspto-grants-2011_03
Patent number
US07902375B2

Reaction notes

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