2-Benzyl-3-cyclobutylisoxazolidin-5-one → 3-Amino-3-cyclobutylpropanoic acid

HRID 1055055Notes

Reaction equation

HRID 1055055 reaction equation
C([N:8]1[CH:12]([CH:13]2[CH2:16][CH2:15][CH2:14]2)[CH2:11][C:10](=[O:17])[O:9]1)C1C=CC=CC=1.[H][H]>C(O)C.O[Pd]O>[NH2:8][CH:12]([CH:13]1[CH2:16][CH2:15][CH2:14]1)[CH2:11][C:10]([OH:17])=[O:9]

Participants

5

Reactant 2

HCID 867147422-Benzyl-3-cyclobutylisoxazolidin-5-one2×HCID 178418361HCID 178418361, compound

Product 1

HCID 247302513-Amino-3-cyclobutylpropanoic acid

Reagents, catalysts & solvents 2

HCID 178526213HCID 178526213, compoundCatalystHCID 702EthanolSolvent

Procedure

Dihydroxypalladium (0.252 g, 1.794 mmol) was charged into a flask and flushed with nitrogen. Ethanol (30 mL) was added followed by a solution of 2-benzyl-3-cyclobutyl-isoxazolidin-5-one, 47a, (0.834 g, 3.605 mmol) in approximately 90 mL of ethanol. The reaction mixture was subjected to 50 psi of hydrogen for 4 hours. The pressure was vented and the catalyst was filtered off. All volatiles were removed at reduced pressure. 1H NMR shows the presence of starting material, 47a. The mixture was dissolved in approximately 100 mL of MeOH and added to 83 mg of 10% Pd/C that had been wet with 20 mL of MeOH. The mixture was subjected to 50 psi of H2 overnight. The pressure was vented and the catalyst was filtered off. All volatiles were removed at reduced pressure to afford 340 mg of product. The resulting crude residue was used without further purification: 1H NMR (400 MHz, d6-DMSO) δ 3.06-2.83 (m, 1H), 2.28 (ddd, J=23.7, 11.8, 7.7 Hz, 1H), 2.19-1.99 (m, 2H), 1.99-1.56 (m, 6H).

Workup

  1. customflushed with nitrogen
  2. additionEthanol (30 mL) was added
  3. filtrationthe catalyst was filtered off
  4. customAll volatiles were removed at reduced pressure
  5. dissolutionThe mixture was dissolved in approximately 100 mL of MeOH
  6. additionadded to 83 mg of 10% Pd/C that
  7. customwas subjected to 50 psi of H2 overnight
  8. filtrationthe catalyst was filtered off
  9. customAll volatiles were removed at reduced pressure

Sources & evidence

ORD record
ord-8026c9328948493fb095f919379a98a5
Source dataset
uspto-grants-2016_07
Patent number
US09394302B2

Reaction notes

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