Imidazole → 1-Benzyl-4-iodomethyl-pyrrolidin-2-one

HRID 130519Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 130519
[CH2:1]([N:8]1[CH2:12][CH:11]([CH2:13]O)[CH2:10][C:9]1=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[I:40]I>C1(C)C=CC=CC=1>[CH2:1]([N:8]1[CH2:12][CH:11]([CH2:13][I:40])[CH2:10][C:9]1=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 1788241-Benzyl-4-(hydroxymethyl)pyrrolidin-2-one

Produkt 1

HCID 128272761-Benzyl-4-iodomethyl-pyrrolidin-2-oneAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To alcohol lactam 74 (11.18 g, 0.056 mol) in 210 mL toluene was added in turn, triphenylphosphine (20.0 g, 0.076 mol), imidazole (10.8 g, 0.159 mol), and iodine (19.0 g, 0.075 mol). After stirring the suspension for 1.5 hours, the supernatant was poured into another flask. The sticky yellow residue was washed twice with ether and the solutions were combined. The solvent was evaporated and the residue was chromatographed on silica, eluting with 1:1 acetone/hexane to give 7.92 g, 46% of the iodolactam 75 as yellow oil. 1H NMR (CDCl3) δ 7.25 (m, 5H), 4.38 (d, 1H, J=14.6), 4.46 (d, 1H, J=14.6), 3.38 (dd, 1H, J=7.8 and 2.2) 3.20 (dd, 1H, J=5.6 and 4.4), 3.12 (dd, 1H, J=7.3 and 2.4), 2.96 (dd, 1H, J=5.8 and 4.4), 2.60 (m, 2H), 2.22 (dd, 1H, J=10.5 and 9.7). MS, m/z (relative intensity): 224 [M−H—Bn, 94%], 317 [M+2H, 64%]. IR 3027, 2917, 1688, 1438, 1267, and 701 cm−1.

Aufarbeitung

  1. additionthe supernatant was poured into another flask
  2. washThe sticky yellow residue was washed twice with ether
  3. customThe solvent was evaporated
  4. customthe residue was chromatographed on silica
  5. washeluting with 1:1 acetone/hexane

Quellen und Nachweise

ORD-Eintrag
ord-83089a3140724d199d7fa1a02b0badc2
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07381747B2

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