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

HRID 1055054ノート

反応式

HRID 1055054 の反応式
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

参加物

6

反応物 3

HCID 8471TriethylamineHCID 11332622N-benzylhydroxylamine hydrochlorideHCID 57706492(E)-Ethyl 3-cyclobutylacrylate2 回

生成物 1

HCID 867147422-Benzyl-3-cyclobutylisoxazolidin-5-one収率 86%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-d9ad23d5e0aa431a9eb0f8b638535868
出典データセット
uspto-grants-2016_07
特許番号
US09394302B2

反応ノート

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