Trifluoroacetic acid → (4-{2-[5-(4-Acetylpiperazin-1-yl)pyridin-2-yl]ethyl}phenyl)methanol

HRID 1465473ノート

反応式

HRID 1465473 の反応式
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]2[N:16]=[CH:15][C:14]([N:17]3[CH2:22][CH2:21][N:20]([C:23](OC(C)(C)C)=[O:24])[CH2:19][CH2:18]3)=[CH:13][CH:12]=2)=[CH:5][CH:4]=1.F[C:31](F)(F)C(O)=O.C(OC(=O)C)(=O)C.C(N(CC)CC)C>ClCCl.O1CCCC1>[C:23]([N:20]1[CH2:21][CH2:22][N:17]([C:14]2[CH:13]=[CH:12][C:11]([CH2:10][CH2:9][C:6]3[CH:7]=[CH:8][C:3]([CH2:2][OH:1])=[CH:4][CH:5]=3)=[N:16][CH:15]=2)[CH2:18][CH2:19]1)(=[O:24])[CH3:31]

参加物

7

反応物 4

HCID 6422Trifluoroacetic acidHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 67030135Tert-butyl 4-(6-{2-[4-(hydroxymethyl)phenyl]ethyl}pyridin-3-yl)piperazine-1-carboxylate

生成物 1

HCID 58181252(4-{2-[5-(4-Acetylpiperazin-1-yl)pyridin-2-yl]ethyl}phenyl)methanol収率 66.8%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of tert-butyl 4-(6-{2-[4-(hydroxymethyl)phenyl]ethyl}pyridin-3-yl)piperazine-1-carboxylate (198.8 mg, 0.500 mmol) in dichloromethane (3 ml) was added trifluoroacetic acid (3 ml) at room temperature, and the mixture was stirred for 2.5 hrs. The reaction mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate solution was added to the residue, and the mixture was extracted twice with ethyl acetate. The combined organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. Anhydrous tetrahydrofuran (3 ml) was added to the residue, and acetic anhydride (0.047 ml, 0.50′mmol) and triethylamine (0.069 ml, 0.50 mmol) were added. After stirring at room temperature for 3 hrs, the mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methanol:dichloromethane=1:20→4:10) to give (4-{2-[5-(4-acetylpiperazin-1-yl)pyridin-2-yl]ethyl}phenyl)methanol (113.4 mg, yield 66.8%) as a silghtly yellow solid.

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate solution
  2. additionwas added to the residue
  3. extractionthe mixture was extracted twice with ethyl acetate
  4. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionwere added
  7. stirringAfter stirring at room temperature for 3 hrs
  8. concentrationthe mixture was concentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (methanol:dichloromethane=1:20→4:10)

出典と根拠

ORDレコード
ord-e74ac341c5454a25ad0dd115b9573db3
出典データセット
uspto-grants-2015_04
特許番号
US08999989B2

反応ノート

読み込み中…