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

HRID 1052892노트

반응식

HRID 1052892 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c8e5f9d616c34af3bb5cdfedb6f0b67d
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09388440B2

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