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

HRID 1052892Notes

Reaction equation

HRID 1052892 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-c8e5f9d616c34af3bb5cdfedb6f0b67d
Source dataset
uspto-grants-2016_07
Patent number
US09388440B2

Reaction notes

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