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Aluminium lithium hydride → 2,6-dichloro-N-[(1R)-2-[2-(2,6-dichlorophenyl)-6-quinolinyl]-1-(hydroxymethyl)ethyl]benzamide

HRID 1869815
ノート
印刷プレビュー

反応式

HRID 1869815 の反応式
[Cl:1][C:2]1[CH:34]=[CH:33][CH:32]=[C:31]([Cl:35])[C:3]=1[C:4]([NH:6][C@H:7]([CH2:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[N:19]=[C:18]([C:23]1[C:28]([Cl:29])=[CH:27][CH:26]=[CH:25][C:24]=1[Cl:30])[CH:17]=[CH:16]2)[C:8](OC)=[O:9])=[O:5].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Cl:1][C:2]1[CH:34]=[CH:33][CH:32]=[C:31]([Cl:35])[C:3]=1[C:4]([NH:6][C@@H:7]([CH2:8][OH:9])[CH2:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[N:19]=[C:18]([C:23]1[C:28]([Cl:29])=[CH:27][CH:26]=[CH:25][C:24]=1[Cl:30])[CH:17]=[CH:16]2)=[O:5]
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 21226445Aluminium lithium hydrideHCID 86619055methyl (2R)-2-[(2,6-dichlorobenzoyl)amino]-3-[2-(2,6-dichlorophenyl)-6-quinolinyl]propanoate

生成物 1

HCID 685938592,6-dichloro-N-[(1R)-2-[2-(2,6-dichlorophenyl)-6-quinolinyl]-1-(hydroxymethyl)ethyl]benzamide収率 62%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To methyl (2R)-2-[(2,6-dichlorobenzoyl)amino]-3-[2-(2,6-dichlorophenyl)-6-quinolinyl]propanoate 36 (0,222 g) in THF (1 ml) is added, at 0° C., LiAlH4 (1.5 equ.). The solution is stirred at 0° C. for 1 hour. The reaction is quenched at −25° C. by successive additions of water (25 μl), 15% NaOH (25 μl) and water (75 μl). After evaporation of THF under vacuum, AcOEt is added. The organic phases are washed with water, brine, dried over MgSO4 and evaporated. The resulting residue is purified over silica gel using CH2Cl2/CH3OH/NH4OH (99/1/0.1) as eluent to give 2,6-dichloro-N-[(1R)-2-[2-(2,6-dichlorophenyl)-6-quinolinyl]-1-(hydroxymethyl)ethyl]benzamide 60.

後処理

  1. customThe reaction is quenched at −25° C. by successive additions of water (25 μl), 15% NaOH (25 μl) and water (75 μl)
  2. customAfter evaporation of THF under vacuum, AcOEt
  3. additionis added
  4. washThe organic phases are washed with water, brine
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. customThe resulting residue is purified over silica gel

出典と根拠

ORDレコード
ord-1c00855592314e91bf7f2012ac816d12
出典データセット
uspto-grants-2009_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07638630B2

反応ノート

読み込み中…

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