Triethylamine → 2-Benzyl-3-cyclobutylisoxazolidin-5-one

HRID 1055054노트

반응식

HRID 1055054 반응식
Cl.[CH2:2]([NH:9][OH:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH:18]1(/[CH:22]=[CH:23]/[C:24](OCC)=[O:25])[CH2:21][CH2:20][CH2:19]1>ClCCl.O>[CH2:2]([N:9]1[CH:22]([CH:18]2[CH2:21][CH2:20][CH2:19]2)[CH2:23][C:24](=[O:25])[O:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 11332622N-benzylhydroxylamine hydrochlorideHCID 57706492(E)-Ethyl 3-cyclobutylacrylate2회

생성물 1

HCID 867147422-Benzyl-3-cyclobutylisoxazolidin-5-one수율 86%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

N-benzylhydroxylamine hydrochloride (0.77 g, 4.82 mmol) and triethylamine (0.76 mL, 5.45 mmol) were successively added to a solution of (E)-ethyl 3-cyclobutylacrylate, 46a, (0.65 g, 4.19 mmol) in dry dichloromethane (23.5 mL). The reaction mixture was allowed to stir at room temperature under an atmosphere of nitrogen for 3 days. The mixture was diluted with 75 mL of water and the layers were separated. The aqueous phase was reextracted twice more with dichloromethane (50 mL). The combined organic phases were dried over MgSO4, filtered and evaporated to dryness. The residue was purified via silica gel chromatography (0-100% EtOAc/Hexanes gradient) to afford 834 mg (86%) of the desired product: 1H NMR (400 MHz, CDCl3) δ 7.38-7.26 (m, 5H), 4.64 (s, 1H), 3.82 (q, J=13.5 Hz, 2H), 3.37-3.18 (m, 1H), 2.80-2.52 (m, 2H), 2.33 (dd, J=14.5, 5.1 Hz, 1H), 2.22-2.09 (m, 1H), 2.01-1.68 (m, 5H).

후처리

  1. customthe layers were separated
  2. dry with materialThe combined organic phases were dried over MgSO4
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe residue was purified via silica gel chromatography (0-100% EtOAc/Hexanes gradient)

출처 및 근거

ORD 기록
ord-d9ad23d5e0aa431a9eb0f8b638535868
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394302B2

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