3-Chlorophenol → (+/-)-(4R* 5R*)-5-[(3-chlorophenoxy)methyl]-1-methyl-4-phenylpyrrolidin-2-one

HRID 1837986Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1837986
[OH:1][CH2:2][C@@H:3]1[N:7]([CH3:8])[C:6](=[O:9])[CH2:5][C@@H:4]1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl:35][C:36]1[CH:37]=[C:38](O)[CH:39]=[CH:40][CH:41]=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[Cl:35][C:36]1[CH:41]=[C:40]([CH:39]=[CH:38][CH:37]=1)[O:1][CH2:2][C@@H:3]1[N:7]([CH3:8])[C:6](=[O:9])[CH2:5][C@@H:4]1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Komponenten

6

Edukt 4

HCID 79333-ChlorophenolHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 13825981(4R,5R)-5-(hydroxymethyl)-1-methyl-4-phenylpyrrolidin-2-one2×

Produkt 1

HCID 69891684(+/-)-(4R* 5R*)-5-[(3-chlorophenoxy)methyl]-1-methyl-4-phenylpyrrolidin-2-oneAusbeute 23 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of (±)-(4R*,5R*)-5-(hydroxymethyl)-1-methyl-4-phenylpyrrolidin-2-one (Intermediate T prepared by Method 2, 220 mg, 1.1 mmol), PPh3 (422 mg, 1.6 mmol) and 3-chlorophenol (0.13 mL, 1.6 mmol) in THF (10 mL) was added DIAD (0.31 mL, 1.6 mmol). The reaction mixture was stirred overnight, then concentrated under reduced pressure and purified by flash chromatography (30% EtOAc/CH2Cl2) to afford (±)-(4R*,5R*)-5-[(3-chlorophenoxy)methyl]-1-methyl-4-phenylpyrrolidin-2-one (80 mg, 23%) as a colorless oil. TLC (75% EtoAc/25% hexanes) Rf 0.29, CI m/z (rel abundance) 316 ([MH]+, 100%).

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. custompurified by flash chromatography (30% EtOAc/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-f89e49e805104be582a852189774e00c
Quelldatensatz
uspto-grants-2004_08
Patentnummer
US06784167B2

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