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

HRID 2171852노트

반응식

HRID 2171852 반응식
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]

참가 물질

5

반응물 2

HCID 867147422-Benzyl-3-cyclobutylisoxazolidin-5-one2회HCID 178418361HCID 178418361, 화합물

생성물 1

HCID 247302513-Amino-3-cyclobutylpropanoic acid

시약·촉매·용매 2

HCID 178526213HCID 178526213, 화합물촉매HCID 702Ethanol용매

실험 절차

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-cyclobutylisoxazolidin-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).

후처리

  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

출처 및 근거

ORD 기록
ord-1e0a058785964adf89da9d44dd19af03
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09051319B2

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