(-)-Diisopinocampheyl chloroborane → 1-(4-Fluoro-phenyl)-5-hydroxy-5-morpholin-4-yl-pentan-1-one

HRID 1052892ノート

反応式

HRID 1052892 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:20])[CH2:9][CH2:10][CH2:11][C:12]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[O:13])=[CH:4][CH:3]=1.B(Cl)(C1C(C)C2C(C)(C)C(C2)C1)C1C(C)C2C(C)(C)C(C2)C1>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:20])[CH2:9][CH2:10][CH2:11][CH:12]([OH:13])[N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 4076588(-)-Diisopinocampheyl chloroboraneHCID 580708091-(4-Fluorophenyl)-5-(morpholin-4-yl)pentane-1,5-dione

生成物 1

HCID 667135681-(4-Fluoro-phenyl)-5-hydroxy-5-morpholin-4-yl-pentan-1-one収率 54.6%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

10 gms of 1-(4-Fluoro-phenyl)-5-morpholin-4-yl-pentane-1,5-dione was taken in 62 ml of toluene to this 46 ml of (−)-Diisopinocampheyl chloroborane (DIP chloride) solution was added at 0-5° C. Stirred the reaction mass for about 6 hours and quenched the reaction mass with 750 ml of 10% NaOH. To the reaction mass was washed with brine solution. Washed the obtained organic layer with ammonium chloride solution and dried over sodium sulphate. Distilled the solvent and isolated through column chromatography to get 5.5 gms of 1-(4-Fluoro-phenyl)-5-hydroxy-5-morpholin-4-yl-pentan-1-one.

後処理

  1. additionwas added at 0-5° C
  2. customquenched the reaction mass with 750 ml of 10% NaOH
  3. washTo the reaction mass was washed with brine solution
  4. washWashed the obtained organic layer with ammonium chloride solution
  5. dry with materialdried over sodium sulphate
  6. distillationDistilled the solvent
  7. customisolated through column chromatography

出典と根拠

ORDレコード
ord-c8e5f9d616c34af3bb5cdfedb6f0b67d
出典データセット
uspto-grants-2016_07
特許番号
US09388440B2

反応ノート

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