Sodium Hydroxide → 3-[1,1-Dimethyl-2-(tetrahydropyran-2-yloxy)-ethyl]-isoxazol-5-ylamine

HRID 469757ノート

反応式

HRID 469757 の反応式
S(O)(O)(=O)=O.[OH:6][NH2:7].[CH3:8][C:9]([CH3:23])([CH2:15][O:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][O:18]1)[C:10](=O)[CH2:11][C:12]#[N:13].[OH-].[Na+]>O>[CH3:8][C:9]([C:10]1[CH:11]=[C:12]([NH2:13])[O:6][N:7]=1)([CH3:23])[CH2:15][O:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][O:18]1

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 159255Hydroxylamine, sulfate (1:1)HCID 592532944,4-Dimethyl-3-oxo-5-(tetrahydro-pyran-2-yloxy)-pentanenitrile

生成物 1

HCID 592532173-[1,1-Dimethyl-2-(tetrahydropyran-2-yloxy)-ethyl]-isoxazol-5-ylamine

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

Hydroxyamine sulfate (0.729 g, 4.439 mmol) is added to a stirred solution of 4,4-dimethyl-3-oxo-5-(tetrahydro-pyran-2-yloxy)-pentanenitrile (2 g, 8.878 mmol) and sodium hydroxide (0.764 g, 19.1 mmol) in water (20 mL). The reaction mixture is stirred at reflux for 18 hours. After this time, the reaction mixture is cooled to room temperature and extracted with ethyl acetate. The organic layers are combined and washed with brine, dried (Na2SO4), filtered and concentrated to yield the title compound, m/z 157 [M+H+−84]. 1H NMR (400 MHz, DMSO-d) δ ppm 1.17 (6H, d), 1.45 (4H, br), 1.58 (1H, br), 1.68 (1H, br), 3.26 (1H, d), 3.4 (1H, br), 3.59 (1H, d), 3.68 (1H, br), 4.5 (1H, br), 4.88 (1H, s), 6.43 (2H, s).

後処理

  1. temperatureat reflux for 18 hours
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-f5127ba1008b4e52ad0041caa6d8d8a7
出典データセット
uspto-grants-2014_01
特許番号
US08629157B2

反応ノート

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