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Benzyl Bromide → (2S)-2-(1-benzyl-1H-1,2,4-triazol-3-yl)-1-[(4-fluorophenyl)sulfonyl]piperidine

HRID 397635
ノート
印刷プレビュー

反応式

HRID 397635 の反応式
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([N:19]2[CH2:24][CH2:23][CH2:22][CH2:21][C@H:20]2[C:25]2[N:29]=[CH:28][NH:27][N:26]=2)(=[O:18])=[O:17])=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:1]([N:27]1[CH:28]=[N:29][C:25]([C@@H:20]2[CH2:21][CH2:22][CH2:23][CH2:24][N:19]2[S:16]([C:13]2[CH:14]=[CH:15][C:10]([F:9])=[CH:11][CH:12]=2)(=[O:17])=[O:18])=[N:26]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=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

5

反応物 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 178527361(2S)-1-[(4-fluorophenyl)sulfonyl]-2-(1H-1,2,4-triazol-3-yl)piperidine

生成物 1

HCID 9930859(2S)-2-(1-benzyl-1H-1,2,4-triazol-3-yl)-1-[(4-fluorophenyl)sulfonyl]piperidine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

Benzyl bromide (40 μl) was added to a solution of (2S)-1-[(4-fluorophenyl)sulfonyl]-2-(1H-1,2,4-triazol-3-yl)piperidine (95 mg) [see Preparation 42] and potassium carbonate (47 mg) in dimethylformamide (5 ml). The reaction mixture was stirred at 50° C. for 7 hours, after which time the solvent was removed under reduced pressure and the residue diluted with ethyl acetate. The organic solution was washed with water, dried over magnesium sulphate and the solvent removed under reduced pressure. The crude product was purified by column chromatography on silica gel eluting with 100:0 changing to 50:50, by volume, hexane:ethyl acetate (in 10% increments), to afford (2S)-2-(1-benzyl-1H-1,2,4-triazol-3-yl)-1-[(4-fluorophenyl)sulfonyl]piperidine (35 mg) as a white solid.

後処理

  1. customafter which time the solvent was removed under reduced pressure
  2. additionthe residue diluted with ethyl acetate
  3. washThe organic solution was washed with water
  4. dry with materialdried over magnesium sulphate
  5. customthe solvent removed under reduced pressure
  6. customThe crude product was purified by column chromatography on silica gel eluting with 100:0 changing to 50:50, by volume, hexane

出典と根拠

ORDレコード
ord-efc57f09127740b395f2744c18aa8300
出典データセット
uspto-grants-2003_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06610707B1

反応ノート

読み込み中…

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