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Acetic Acid → HCID 86682449、化合物

HRID 715874
ノート
印刷プレビュー

反応式

HRID 715874 の反応式
[F:1][C:2]1([F:47])[CH2:7][CH2:6][CH:5]([C:8]2[C:17]3[CH:16]([OH:18])[CH2:15][C:14]([CH3:20])([CH3:19])[CH2:13][C:12]=3[N:11]=[C:10]([CH:21]3[CH2:26][CH2:25][N:24]([C:27]4[N:32]=[CH:31][C:30](C=O)=[CH:29][N:28]=4)[CH2:23][CH2:22]3)[C:9]=2[CH:35]([F:46])[C:36]2[CH:41]=[CH:40][C:39]([C:42]([F:45])([F:44])[F:43])=[CH:38][CH:37]=2)[CH2:4][CH2:3]1.[C:48]([OH:51])(=O)[CH3:49].[CH3:52][NH:53][CH2:54]CO.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>O1CCCC1>[F:1][C:2]1([F:47])[CH2:3][CH2:4][CH:5]([C:8]2[C:17]3[CH:16]([OH:18])[CH2:15][C:14]([CH3:20])([CH3:19])[CH2:13][C:12]=3[N:11]=[C:10]([CH:21]3[CH2:26][CH2:25][N:24]([C:27]4[N:32]=[CH:31][C:30]([CH2:52][N:53]([CH2:49][CH2:48][OH:51])[CH3:54])=[CH:29][N:28]=4)[CH2:23][CH2:22]3)[C:9]=2[CH:35]([F:46])[C:36]2[CH:41]=[CH:40][C:39]([C:42]([F:45])([F:43])[F:44])=[CH:38][CH:37]=2)[CH2:6][CH2:7]1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 176Acetic AcidHCID 80162-(Methylamino)ethanolHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 86682450HCID 86682450、化合物

生成物 1

HCID 86682449HCID 86682449、化合物収率 89%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 70 mg (0.11 mmol) of 4-(4,4-Difluorocyclohexyl)-3-{fluoro[4-(trifluoromethyl)phenyl]methyl}-2-[1-(5-formyl pyrimidin-2-yl)piperidin-4-yl]-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-5-ol obtained in Example (36-1) in 1.0 ml of tetrahydrofuran, 6.1 μl (0.11 mmol) of acetic acid, 26 μl (0.32 mmol) of 2-(methylamino)ethanol and 68 mg (0.32 mmol) of sodium triacetoxyborohydride were added, and the reaction solution was stirred at room temperature for 3 hours. After completion of the reaction, saturated sodium hydrogencarbonate aqueous solution was added to the reaction solution and the reaction solution was extracted with dichloromethane. The organic layer was dried with anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was subjected to silica gel column chromatography [dichloromethane/methanol/28% ammonia aqueous solution=95/4.75/0.25-80/19/1 (V/V/V)] to provide 68 mg of the title compound as a white solid (yield: 89%).

後処理

  1. additionwas added to the reaction solution
  2. extractionthe reaction solution was extracted with dichloromethane
  3. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure

出典と根拠

ORDレコード
ord-fbb991cb11e24532905683d86dfbd679
出典データセット
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09187450B2

反応ノート

読み込み中…

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