Ammonium Chloride → (+/-)-(4R*,5R*)-5-((1S *)-Hydroxy-2-thienylmethyl)-1-methyl4-phenyl-pyrrolidin-2-one

HRID 1837990Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1837990
[S:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[Li].[CH:7]([C@@H:9]1[N:13]([CH3:14])[C:12](=[O:15])[CH2:11][C@@H:10]1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:8].[NH4+].[Cl-]>C1COCC1>[OH:8][C@H:7]([C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)[C@@H:9]1[N:13]([CH3:14])[C:12](=[O:15])[CH2:11][C@@H:10]1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 13825985(-)-(4R*,5R*)-5-formyl-1-methyl-4-phenylpyrrolidin-2-one2×HCID 68750865Lithium Thiophene

Produkt 1

HCID 14071421(+/-)-(4R*,5R*)-5-((1S *)-Hydroxy-2-thienylmethyl)-1-methyl4-phenyl-pyrrolidin-2-oneAusbeute 27 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a −50° C. solution of lithium thiophene (1M in THF, 170 mL, 170 mmol) was added a solution of (±)-(4R*,5R*)-5-formyl-1-methyl-4-phenylpyrrolidin-2-one (Intermediate Z, 127 mmol) in THF (10 mL). The reaction mixture was allowed to warm to 0° C. over 45 min and treated with a saturated NH4Cl solution. The resulting mixture was extracted with EtOAc, dried (MgSO4) and concentrated under reduced pressure. The crude product was purified by flash chromatography (67% EtOAc/hex) to give (±)-(4R*,5R*)-5-((1S*)-hydroxy-2-thienylmethyl)-1-methyl-4-phenylpyrrolidin-2-one (9.76 g, 27%): TLC (EtOAc) Rf 0.42.

Aufarbeitung

  1. extractionThe resulting mixture was extracted with EtOAc
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was purified by flash chromatography (67% EtOAc/hex)

Quellen und Nachweise

ORD-Eintrag
ord-a204989fae014c6f9382e8d6ac9655c6
Quelldatensatz
uspto-grants-2004_08
Patentnummer
US06784167B2

Notizen zur Reaktion

Wird geladen…