Carbon tetrabromide → 1-(2-Bromoethyl)-3,3-diphenylpyrrolidin-2-one

HRID 1667134

Reaktionsgleichung

Reaktionsgleichung von HRID 1667134
O[CH2:2][CH2:3][N:4]1[CH2:8][CH2:7][C:6]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5]1=[O:21].C(Br)(Br)(Br)[Br:23].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:23][CH2:2][CH2:3][N:4]1[CH2:8][CH2:7][C:6]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5]1=[O:21]

Komponenten

5

Edukt 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 673575371-(2-Hydroxyethyl)-3,3-diphenylpyrrolidin-2-one

Produkt 1

HCID 673587991-(2-Bromoethyl)-3,3-diphenylpyrrolidin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of the product from Example 64A (0.3, 1.1 mmol) in methylene chloride was added carbon tetrabromide (0.7 g, 2.13 mmol) and triphenylphosphine (0.56 g, 2.13 mmol) and the reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated, and the obtained residue was chromatographed on silica gel eluting with 10-30% ethyl acetate/hexane to yield the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.31 (m, 10H), 3.78 (t, J=6.44 Hz, 2H), 3.54 (t, J=5.59 Hz, 2H), 3.49 (t, J=5.76 Hz, 2H), 2.80 (t, J=6.44 Hz, 2H); MS (ESI+) m/z 345 (M+H)+.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. customthe obtained residue was chromatographed on silica gel eluting with 10-30% ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-86881dcc2e0e4a86a5db31abf03f66a3
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08044069B2

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