Water → 2-(5-Methyl-1,2,4-oxadiazol-3-yl)propan-2-amine

HRID 632015Notes

Reaction equation

HRID 632015 reaction equation
C(OC(=O)[NH:7][C:8]([C:11]1[N:15]=[C:14]([CH3:16])[O:13][N:12]=1)([CH3:10])[CH3:9])(C)(C)C.O>C(OCC)(=O)C.Cl>[CH3:9][C:8]([CH3:10])([C:11]1[N:15]=[C:14]([CH3:16])[O:13][N:12]=1)[NH2:7]

Participants

5

Reactant 2

HCID 962WaterHCID 71113127tert-Butyl 2-(5-methyl-1,2,4-oxadiazol-3-yl)propan-2-ylcarbamate

Product 1

HCID 435592512-(5-Methyl-1,2,4-oxadiazol-3-yl)propan-2-amine

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl-2-(5-methyl-1,2,4-oxadiazol-3-yl)propan-2-ylcarbamate (5.38 g) was dissolved in in ethyl acetate (30 mL) saturated with hydrochloride and stirred at room temperature for 1 h. Then water (50 mL) was added. The aqueous phase was washed with ethyl acetate (2×30 mL) and the pH adjusted with 1 M sodium hydroxide solution to 9˜10. The solution was extracted with ethyl acetate (2×30 mL). The combined extracts were washed with brine and dried over anhydrous sodium sulfate. Removal of the solvent under reduced pressure left the title compound (1.7 g, 54%) as colorless oil; MS: m/e 142.2 [M+H]+.

Workup

  1. washThe aqueous phase was washed with ethyl acetate (2×30 mL)
  2. extractionThe solution was extracted with ethyl acetate (2×30 mL)
  3. washThe combined extracts were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customRemoval of the solvent under reduced pressure
  6. waitleft the title compound (1.7 g, 54%) as colorless oil

Sources & evidence

ORD record
ord-4edb0cb5bcbf48feacb9a3f7d7eab9f2
Source dataset
uspto-grants-2016_04
Patent number
US09321727B2

Reaction notes

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