Chloride → 1-Benzyl-5-biphenyl-4-ylmethyl-5-hydroxy-pyrrolidin-2-one

HRID 1021063

Reaktionsgleichung

Reaktionsgleichung von HRID 1021063
[CH2:1]([N:8]1[C:12](=[O:13])[CH2:11][CH2:10][C:9]1=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Cl-].[NH4+].[CH2:18]1[CH2:22]O[CH2:20][CH2:19]1>>[CH2:1]([N:8]1[C:12]([CH2:20][C:19]2[CH:20]=[CH:19][C:18]([C:22]3[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=3)=[CH:22][CH:18]=2)([OH:13])[CH2:11][CH2:10][C:9]1=[O:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 4

HCID 312ChlorideHCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 952411-(Phenylmethyl)-2,5-pyrrolidinedione

Produkt 1

HCID 593184651-Benzyl-5-biphenyl-4-ylmethyl-5-hydroxy-pyrrolidin-2-one

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

9.5 g N-Benzylsuccinimide is added to 120 ml THF and the mixture is then cooled to −78° C. A solution of 4-methylbiphenylmagnesium chloride in THF (1.3 eq) is then added. The subsequent mixture is then stirred for 2 h at −78° C. The mixture is then warmed to 10° C. and 100 ml saturated ammonium chloride solution is added. The phases are separated and the aqueous phase is extracted with toluene. The combined organic phases are washed with water then brine and then concentrated in vacuo. The crude material is crystallized from toluene to give 1-Benzyl-5-biphenyl-4-ylmethyl-5-hydroxy-pyrrolidin-2-one. 1H NMR (DMSO): 1.72 (1H), 1.91 (1H), 2.27 (2H), 2.72 (1H), 2.97 (2H), 4.40 (1H), 4.55 (1H), 7.21-7.66 (14H).

Aufarbeitung

  1. temperatureThe mixture is then warmed to 10° C.
  2. customThe phases are separated
  3. extractionthe aqueous phase is extracted with toluene
  4. washThe combined organic phases are washed with water
  5. concentrationbrine and then concentrated in vacuo
  6. customThe crude material is crystallized from toluene

Quellen und Nachweise

ORD-Eintrag
ord-54d4e0fc11c94b60b81a3174a2b36bbf
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08716495B2

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