Iodobenzene → 1-Phenylpyrrolidine

HRID 641909

Reaktionsgleichung

Reaktionsgleichung von HRID 641909
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.N1CCC[C@H]1C(O)=O.I[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>[Cu]I.CS(C)=O>[C:15]1([N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Komponenten

6

Edukt 3

HCID 11575IodobenzeneHCID 31268PyrrolidineHCID 145742L-Proline

Produkt 1

HCID 777261-PhenylpyrrolidineAusbeute 59,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Pyrrolidine (21.6 g, 304.23 mmol), L-proline (1.12 g, 9.74 mmol), and CuI (960 mg, 5.05 mmol) were added sequentially to 1-iodobenzene (10.0 g, 49.02 mmol). DMSO (40 mL) was then added, and the resulting solution was stirred at 60° C. for 20 hours. The reaction mixture was then quenched by adding 400 mL of iced water. The resulting solution was extracted with ethyl acetate (3×150 mL), and the organic layers were combined, dried (Na2SO4), filtered and concentrated. The residue was purified by column chromatography using a 1:100 ethyl acetate/petroleum ether solvent system to afford 4.3 g (57%) of 1-phenylpyrrolidine as brown oil.

Aufarbeitung

  1. customThe reaction mixture was then quenched
  2. additionby adding 400 mL of iced water
  3. extractionThe resulting solution was extracted with ethyl acetate (3×150 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-a24edf014d2a41488f03db31dc34e41c
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07696229B2

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