Trifluoroacetic acid → HCID 67441565、化合物

HRID 2045402ノート

反応式

HRID 2045402 の反応式
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]([C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)[C:10]([CH3:23])([CH3:22])[CH:9]2O)=[O:5])[CH3:2].FC(F)(F)C(O)=O>C([SiH](CC)CC)C>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]([C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)[C:10]([CH3:22])([CH3:23])[CH2:9]2)=[O:5])[CH3:2]

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 67441733HCID 67441733、化合物

生成物 1

HCID 67441565HCID 67441565、化合物収率 24.2%

試薬・触媒・溶媒 1

HCID 12052Triethylsilane溶媒

反応条件

温度
25 °C

実験手順

To a mixture of 4-hydroxy-3,3-dimethyl-2-pyridin-3-yl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester (62.5 g, 200 mmol) and triethylsilane (50 mL) at 25° C. was added trifluoroacetic acid (25 mL) dropwise. The resulting mixture was stirred at 25° C. for 4 h. Then the reaction mixture was concentrated in vacuo and the residue was extracted with ethyl acetate (2×200 mL), washed with saturated aqueous sodium bicarbonate solution (2×100 mL), dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was triturated with methanol. The resulting precipitate was collected, dried in vacuo to afford 3,3-dimethyl-2-pyridin-3-yl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester (15 g, 24%) as a white solid: LC/MS m/e calcd for C19H22N2O2 (M+H)+: 311.40, observed: 311.1.

後処理

  1. concentrationThen the reaction mixture was concentrated in vacuo
  2. extractionthe residue was extracted with ethyl acetate (2×200 mL)
  3. washwashed with saturated aqueous sodium bicarbonate solution (2×100 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was triturated with methanol
  7. customThe resulting precipitate was collected
  8. customdried in vacuo

出典と根拠

ORDレコード
ord-d258df6eea1d4c4aa7ea008d1054e983
出典データセット
uspto-grants-2013_11
特許番号
US08586747B2

反応ノート

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