Pyrrolidine → 1-[(4-Bromophenoxy)acetyl]pyrrolidine

HRID 500181

Reaktionsgleichung

Reaktionsgleichung von HRID 500181
C(Cl)(=O)C(Cl)=O.[Br:7][C:8]1[CH:18]=[CH:17][C:11]([O:12][CH2:13][C:14]([OH:16])=O)=[CH:10][CH:9]=1.[NH:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1>C(Cl)Cl.CN(C)C=O>[Br:7][C:8]1[CH:9]=[CH:10][C:11]([O:12][CH2:13][C:14]([N:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)=[O:16])=[CH:17][CH:18]=1

Komponenten

6

Edukt 3

HCID 31268PyrrolidineHCID 65578Oxalyl chlorideHCID 74657p-Bromophenoxyacetic acid

Produkt 1

HCID 7876791-[(4-Bromophenoxy)acetyl]pyrrolidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Oxalyl chloride (0.5 mL, 5.9 mmol) was added to a suspension of (4-bromophenoxy)acetic acid (0.462 g, 2.0 mmol) in methylene chloride (10 mL) and 2 drops of N,N-dimethylformamide. The mixture was stirred at RT for 2 h. The solvent was evaporated under reduced pressure. The residue was diluted with methylene chloride (10 mL), cooled with ice-water bath, and 1M of sodium hydroxide aqueous solution (3.0 mL) was added. To the mixture was added pyrrolidine (167 μL, 2.0 mmol). The mixture was stirred and allowed to warm to RT. The organic layer was separated, washed with water and brine, dried over Na2SO4, filtered, and concentrated. The residue was directly used in next step without further purification (550 mg, 96.7%). LCMS: (M+H)=286.0/284.0

Aufarbeitung

  1. customThe solvent was evaporated under reduced pressure
  2. additionThe residue was diluted with methylene chloride (10 mL)
  3. temperaturecooled with ice-water bath
  4. addition1M of sodium hydroxide aqueous solution (3.0 mL) was added
  5. stirringThe mixture was stirred
  6. temperatureto warm to RT
  7. customThe organic layer was separated
  8. washwashed with water and brine
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe residue was directly used in next step without further purification (550 mg, 96.7%)

Quellen und Nachweise

ORD-Eintrag
ord-746b17a2070148b2ad2b77f13ddfa069
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07767675B2

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