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Citric Acid → 4-(2-Hydroxyethyl)-1-(6-trifluoromethyl benzothiazole-2-yl)piperidine-4-carbonitrile

HRID 420605
ノート
印刷プレビュー

反応式

HRID 420605 の反応式
C([Si](C)(C)[O:6][CH2:7][CH2:8][C:9]1([C:28]#[N:29])[CH2:14][CH2:13][N:12]([C:15]2[S:16][C:17]3[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[CH:20][C:18]=3[N:19]=2)[CH2:11][CH2:10]1)(C)(C)C.[F-].C[N+](C)(C)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>>[OH:6][CH2:7][CH2:8][C:9]1([C:28]#[N:29])[CH2:14][CH2:13][N:12]([C:15]2[S:16][C:17]3[CH:23]=[C:22]([C:24]([F:26])([F:27])[F:25])[CH:21]=[CH:20][C:18]=3[N:19]=2)[CH2:11][CH2:10]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 3

HCID 311Citric AcidHCID 67803Tetramethylammonium fluorideHCID 579664524-[2-(t-Butyldimethyl silyloxy)ethyl]-1-(6-trifluoromethyl benzothiazole-2-yl)piperidine-4-carbonitrile

生成物 1

HCID 579665674-(2-Hydroxyethyl)-1-(6-trifluoromethyl benzothiazole-2-yl)piperidine-4-carbonitrile収率 95%

反応条件

温度
0 °C

実験手順

To 4-[2-(t-butyldimethyl silyloxy)ethyl]-1-(6-trifluoromethyl benzothiazole-2-yl)piperidine-4-carbonitrile (510 mg) was added tetramethylammonium fluoride (1 M tetrahydrofuran solution, 1.63 mL). The mixture was stirred at 0° C. for 0.5 hour. To the reaction solution was added aqueous citric acid solution and extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over sodium sulphate. The solvent was evaporated under reduced pressure and the residue was purified by column chromatograph on silica gel to give the title compound (366 mg). Yield: 95%.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over sodium sulphate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by column chromatograph on silica gel

出典と根拠

ORDレコード
ord-3f30962b45294306898de9dec91c9712
出典データセット
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08097610B2

反応ノート

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