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Tetrabutylammonium Fluoride → (S)-4-(4-fluoro-phenyl)-6-oxo-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid {5-[1-(2-hydroxy-ethyl)-5-methyl-1H-pyrazol-3-yl]-2-methyl-phenyl}-amide

HRID 1697882
ノート
印刷プレビュー

反応式

HRID 1697882 の反応式
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C([Si](C)(C)[O:24][CH2:25][CH2:26][N:27]1[C:31]([CH3:32])=[CH:30][C:29]([C:33]2[CH:34]=[CH:35][C:36]([CH3:56])=[C:37]([NH:39][C:40]([C:42]3[C@H:47]([C:48]4[CH:53]=[CH:52][C:51]([F:54])=[CH:50][CH:49]=4)[CH2:46][C:45](=[O:55])[NH:44][CH:43]=3)=[O:41])[CH:38]=2)=[N:28]1)(C)(C)C>C1COCC1>[OH:24][CH2:25][CH2:26][N:27]1[C:31]([CH3:32])=[CH:30][C:29]([C:33]2[CH:34]=[CH:35][C:36]([CH3:56])=[C:37]([NH:39][C:40]([C:42]3[C@H:47]([C:48]4[CH:49]=[CH:50][C:51]([F:54])=[CH:52][CH:53]=4)[CH2:46][C:45](=[O:55])[NH:44][CH:43]=3)=[O:41])[CH:38]=2)=[N:28]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 67277422(S)-4-(4-Fluoro-phenyl)-6-oxo-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid (5-{1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-methyl-1H-pyrazol-3-yl}-2-methyl-phenyl)-amide

生成物 1

HCID 53239311(S)-4-(4-fluoro-phenyl)-6-oxo-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid {5-[1-(2-hydroxy-ethyl)-5-methyl-1H-pyrazol-3-yl]-2-methyl-phenyl}-amide収率 45.6%

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

反応条件

温度
0 °C

実験手順

A solution tetrabutylammonium fluoride (1M in THF) was added drop wise to a 0° C. solution of (S)-4-(4-Fluoro-phenyl)-6-oxo-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid (5-{1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-methyl-1H-pyrazol-3-yl}-2-methyl-phenyl)-amide (66 mg) in THF. The mixture was stirred at 0° C. for five minutes and then stirred at room temperature for 18 hours. The mixture was partitioned between water and EtOAc. The organic layer was washed with water and brine, dried over Na2SO4, filtered, and concentrated to dryness under reduced pressure. Purification of the crude product by flash chromatography (0 to 8% CH3OH in CH2Cl2) gave 24 mg of (S)-4-(4-fluoro-phenyl)-6-oxo-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid {5-[1-(2-hydroxy-ethyl)-5-methyl-1H-pyrazol-3-yl]-2-methyl-phenyl}-amide as a solid, MS (M+H)=419.

後処理

  1. stirringstirred at room temperature for 18 hours
  2. customThe mixture was partitioned between water and EtOAc
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure
  7. customPurification of the crude product by flash chromatography (0 to 8% CH3OH in CH2Cl2)

出典と根拠

ORDレコード
ord-149fde5200004f31b68db31919296133
出典データセット
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08163929B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート