Sodium hydride → HCID 90065712, compound

HRID 522254Notes

Reaction equation

HRID 522254 reaction equation
[H-].[Na+].[OH:3][CH2:4][CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1.[Br:19][C:20]1[CH:25]=[CH:24][C:23](F)=[C:22]([S:27]([CH3:30])(=[O:29])=[O:28])[CH:21]=1.[Cl-].[NH4+]>CN(C=O)C.CCOC(C)=O>[Br:19][C:20]1[CH:25]=[CH:24][C:23]([O:3][CH2:4][CH2:5][CH:6]2[CH2:7][CH2:8][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:10][CH2:11]2)=[C:22]([S:27]([CH3:30])(=[O:29])=[O:28])[CH:21]=1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 8541401-(tert-Butoxycarbonyl)-4-(2-hydroxyethyl)piperidineHCID 269854244-Bromo-1-fluoro-2-(methylsulphonyl)benzene

Product 1

HCID 90065712HCID 90065712, compoundYield 92.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

After 60% sodium hydride (17 mg) was added to a solution of tert-butyl 4-(2-hydroxyethyl)piperidine-1-carboxylate (109 mg) in DMF (2 mL) at 0° C. in a nitrogen atmosphere, the mixture was stirred at room temperature for 30 minutes. After the reaction mixture was cooled to 0° C., 4-bromo-1-fluoro-2-(methylsulfonyl)benzene (100 mg) was added thereto. The reaction mixture was stirred at 0° C. for 30 minutes, and stirred at room temperature for 3 hours. After a saturated aqueous ammonium chloride solution was added to the reaction mixture, extraction thereof was performed using EtOAc, and the extract was washed with water and saturated brine. The organic layer was dried over Na2SO4 and filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Hex:EtOAc=80:20 to 55:45), whereby tert-butyl 4-{2-[4-bromo-2-(methylsulfonyl)phenoxy]ethyl}piperidine-1-carboxylate (169 mg) was obtained as a colorless liquid.

Workup

  1. temperatureAfter the reaction mixture was cooled to 0° C.
  2. stirringThe reaction mixture was stirred at 0° C. for 30 minutes
  3. stirringstirred at room temperature for 3 hours
  4. washthe extract was washed with water and saturated brine
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (Hex:EtOAc=80:20 to 55:45)

Sources & evidence

ORD record
ord-34c28d6cebee452ea5851a8ab7171e88
Source dataset
uspto-grants-2016_05
Patent number
US09328118B2

Reaction notes

Loading…