Phthalimide → HCID 1296952, Verbindung

HRID 1360190Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1360190
[C@H:1]12[CH2:7][C@H:4]([CH2:5][CH2:6]1)[CH2:3][C@@H:2]2O.[C:9]1(=[O:19])[NH:13][C:12](=[O:14])[C:11]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:10]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[C@H:1]12[CH2:7][C@H:4]([CH2:5][CH2:6]1)[CH2:3][C@H:2]2[N:13]1[C:9](=[O:19])[C:10]2[C:11](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:12]1=[O:14]

Komponenten

6

Edukt 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 10975445endo-Norborneol

Produkt 1

HCID 1296952HCID 1296952, VerbindungAusbeute 65,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of (1R,2S,4S)-bicyclo[2.2.1]heptane-2-ol (1.0 g) in tetrahydrofuran (10 ml) were added phthalimide (1.4 g) and triphenylphosphine (2.6 g), and diethylazodicarboxylate (1.5 ml) dropwise under ice cooling. The mixture was warmed to ambient temperature and stirred for 24 hours. The reaction solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate)=100:0 to 95:5) to obtain 2-[(1R,2R,4S)-bicyclo[2.2.1]hept-2-yl]-1H-isoindole-1,3(2H)-dione (1.4 g) as a colorless solid.

Aufarbeitung

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate)=100:0 to 95:5)

Quellen und Nachweise

ORD-Eintrag
ord-86b7f939950a428da1dc2a45d7cf67e9
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07879844B2

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