Ammonium Acetate → (E)-5-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-enyl)-2,3-dihydro-1H-inden-1-amine

HRID 1502693ノート

反応式

HRID 1502693 の反応式
[F:1][C:2]([F:26])([F:25])[CH:3]([C:16]1[CH:21]=[C:20]([Cl:22])[C:19]([Cl:23])=[C:18]([Cl:24])[CH:17]=1)/[CH:4]=[CH:5]/[C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[C:11](=O)[CH2:10][CH2:9]2.C([O-])(=O)C.[NH4+].C([BH3-])#[N:33].[Na+]>CO>[F:1][C:2]([F:26])([F:25])[CH:3]([C:16]1[CH:21]=[C:20]([Cl:22])[C:19]([Cl:23])=[C:18]([Cl:24])[CH:17]=1)/[CH:4]=[CH:5]/[C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[CH:11]([NH2:33])[CH2:10][CH2:9]2

参加物

5

反応物 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 86675152(E)-5-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-enyl)-2,3-dihydro-1H-inden-1-one

生成物 1

HCID 86675158(E)-5-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-enyl)-2,3-dihydro-1H-inden-1-amine収率 49.7%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a stirred solution of (E)-5-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-enyl)-2,3-dihydro-1H-inden-1-one (1 g, 2.39 mmol) in MeOH (10 mL) were added ammonium acetate (1.84 g, 23.9 mmol) and sodium cyanoborohydride (NaCNBH3; 0.44 g, 7.17 mmol,) and the reaction mixture was heated at reflux for 16 h. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with H2O and extracted with EtOAc. The combined organic extracts were washed with H2O and saturated aqueous sodium bicarbonate (satd aq NaHCO3) solution, dried over anhydrous Na2SO4, and concentrated under reduced pressure to afford the title compound as a liquid (500 mg, crude): 1H NMR (400 MHz, DMSO-d6) δ 7.85 (s, 2H), 7.40 (s, 1H), 7.30 (s, 2H), 6.71 (s, 2H), 4.78 (m, 1H), 4.2 (m, 1H), 2.80 (m, 1H), 2.73 (m, 1H), 1.60 (m, 2H); ESIMS m/z 419.02 ([M+H]+); IR (thin film) 2924, 1552, 1112, 807 cm−1.

後処理

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 16 h
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionthe residue was diluted with H2O
  5. extractionextracted with EtOAc
  6. washThe combined organic extracts were washed with H2O and saturated aqueous sodium bicarbonate (satd aq NaHCO3) solution
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-172f32b1160741ffb7f9ca9f4c6ad580
出典データセット
uspto-grants-2015_12
特許番号
US09210927B2

反応ノート

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