4-Chloroanisole → Pyrrolidine, 1-(4-methoxyphenyl)-

HRID 1354932Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1354932
Cl[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[NH:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1.CC([O-])(C)C.[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:3][CH:4]=1

Komponenten

6

Edukt 3

HCID 121674-ChloroanisoleHCID 31268PyrrolidineHCID 23676156Sodium t-butoxide

Produkt 1

HCID 143187Pyrrolidine, 1-(4-methoxyphenyl)-Ausbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

An oven dried test tube was charged with Pd2(dba)3 (4.5 mg, 0.005 mmol), 27 (7.4 mg, 0.015 mmol), 4-chloroanisole (140 mg, 0.98 mmol), pyrrolidine (85 mg, 1.2 mmol), NaOt-Bu (135 mg, 1.4 mmol), toluene (2 mL), and purged with argon. The mixture was heated to 80° C. and stirred for 18 hours. The reaction mixture was cooled to room temperature, diluted with ether (5 mL), filtered through a plug of celite, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel to give 165 mg (95%) of the title product as colorless crystals.

Aufarbeitung

  1. customAn oven dried test tube
  2. custompurged with argon
  3. temperatureThe reaction mixture was cooled to room temperature
  4. additiondiluted with ether (5 mL)
  5. filtrationfiltered through a plug of celite
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-ce086578f228455aa3ab9a3be0df9545
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07223879B2

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