3-(Trifluoromethyl)benzyl chloride → 5-[3-Oxo-4-(3-trifluoromethyl-phenyl)-butyl]-pyrrolidin-2-one

HRID 352578

Reaktionsgleichung

Reaktionsgleichung von HRID 352578
[Mg].[O:2]=[C:3]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=1)[CH2:4][CH2:5][CH:6]1[NH:10][C:9](=[O:11])[CH2:8][CH2:7]1.FC(F)(F)C1C=C(C=CC=1)CCl.C1C2N(C(=O)CC2)C(=O)C1>CCOCC.C(Cl)Cl>[O:2]=[C:3]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:20])[F:21])[CH:14]=1)[CH2:4][CH2:5][CH:6]1[NH:10][C:9](=[O:11])[CH2:8][CH2:7]1

Komponenten

6

Edukt 3

HCID 697163-(Trifluoromethyl)benzyl chlorideHCID 71893RolziracetamHCID 692674185-[3-Oxo-4-(3-trifluoromethyl-phenyl)-butyl]-pyrrolidin-2-one Magnesium

Produkt 1

HCID 129700875-[3-Oxo-4-(3-trifluoromethyl-phenyl)-butyl]-pyrrolidin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittel2×HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

5-[3-Oxo-4-(3-trifluoromethyl-phenyl)-butyl]-pyrrolidin-2-one Magnesium coils (1.13 g) were stirred under vacuum in a round bottom flask for 60 h. Anhydrous Et2O (5 mL) was added and the reaction mixture was cooled to 0° C. A solution of 3-trifluoromethylbenzyl chloride (1.0 mL, 7.5 mmol) in Et2O (25 mL) was added dropwise over 3 h. The reaction mixture was stirred for an additional 2.5 h. The solution was slowly added via a syringe and filtered through a Nylon Acrodisc™ syringe filter into a solution of tetrahydro-pyrrolizine-3,5-dione (650 mg, 4.68 mmol) in CH2Cl2 (30 mL) at 0° C. After 2 h, the reaction mixture was quenched with 1N HCl and the aqueous solution was washed with CH2Cl2 (2×). The organic solutions were combined, dried (MgSO4), filtered and concentrated. Medium pressure chromatography (1:1 hexanes:EtOAc) provided 5-[3-oxo-4-(3-trifluoromethyl-phenyl)-butyl]-pyrrolidin-2-one (1.376 g). 1H NMR (CDCl3) δ7.38 (m, 4H), 3.78 (s, 2H), 3.61 (m, 1H), 2.58 (t, 2H), 2.30 (m, 2H), 2.20 (m, 1H), 2.86-1.59 (m, 3H).

Aufarbeitung

  1. stirringThe reaction mixture was stirred for an additional 2.5 h
  2. additionThe solution was slowly added via a syringe
  3. filtrationfiltered through a Nylon Acrodisc™ syringe
  4. waitAfter 2 h
  5. customthe reaction mixture was quenched with 1N HCl
  6. washthe aqueous solution was washed with CH2Cl2 (2×)
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-145902757934418c9ad4fb9bcd1c9683
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06747054B2

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