Iodine → (+/-)-(4R*,5R*)-5-[(1R*)-2-(3-chlorophenyl)-1-hydroxyethyl]-1-methyl-4-phenylpyrrolidin-2-one

HRID 1837996Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1837996
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5]Br.II.[CH:12]([C@@H:14]1[N:18]([CH3:19])[C:17](=[O:20])[CH2:16][C@@H:15]1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:13].[NH4+].[Cl-]>CCOCC.C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:5][C@H:12]([C@@H:14]2[N:18]([CH3:19])[C:17](=[O:20])[CH2:16][C@@H:15]2[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[OH:13])[CH:7]=[CH:8][CH:9]=1

Komponenten

7

Edukt 4

HCID 807IodineHCID 25517Ammonium ChlorideHCID 698381-(Bromomethyl)-3-chlorobenzene2×HCID 13825985(-)-(4R*,5R*)-5-formyl-1-methyl-4-phenylpyrrolidin-2-one2×

Produkt 1

HCID 59066522(+/-)-(4R*,5R*)-5-[(1R*)-2-(3-chlorophenyl)-1-hydroxyethyl]-1-methyl-4-phenylpyrrolidin-2-oneAusbeute 34,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A portion of a mixture of 3-chlorobenzyl bromide (0.53 mL, 4.0 mmol) and Et2O (0.5 mL) was added to Mg turnings and I2 (catalytic amount) in Et2O (4 mL). Once the reaction was initiated, the rest of the 3-chlorobenzyl bromide was added. When the reaction subsided, the resulting green mixture was transferred into a −78° C. suspension of CeCl3 (1.05 g, 4.3 mmol) in THF (4 mL). A solution of the (±)-(4R*,5R*)-5-formyl-1-methyl-4-phenylpyrrolidin-2-one (Intermediate Z, 1M in THF, 3 mL, 3 mmol) was added and the reaction mixture was allowed to warm to room temperature, then was treated with a saturated NH4Cl solution and extracted with EtOAc. The combined organic layers were washed with water and a saturated NaCl solution, dried (Na2SO4) and concentrated under reduced pressure. The crude green oil was purified by flash chromatography (EtOAc) to give (±)-(4R*,5R*)-5-[(1R*)-2-(3-chlorophenyl)-1-hydroxyethyl]-1-methyl-4-phenylpyrrolidin-2-one (340 mg, 34%): mp 50-52° C.; TLC (EtOAc) Rf 0.25.

Aufarbeitung

  1. customwas transferred into a −78° C.
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with water
  4. dry with materiala saturated NaCl solution, dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe crude green oil was purified by flash chromatography (EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-8463fd54664e4237a63bf583075200e3
Quelldatensatz
uspto-grants-2004_08
Patentnummer
US06784167B2

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