Phthalimide → 2-Phthalimidomethyl-6-(4-dipropylaminobutyl)naphthalene

HRID 1174004

Reaktionsgleichung

Reaktionsgleichung von HRID 1174004
O[CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH2:13][CH2:14][CH2:15][CH2:16][N:17]([CH2:21][CH2:22][CH3:23])[CH2:18][CH2:19][CH3:20])[CH:9]=2)[CH:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:43]1(=[O:53])[NH:47][C:46](=[O:48])[C:45]2=[CH:49][CH:50]=[CH:51][CH:52]=[C:44]12.N(C(OCC)=O)=NC(OCC)=O.C1(C)C=CC=CC=1>C1COCC1>[C:43]1(=[O:53])[N:47]([CH2:2][C:3]2[CH:12]=[CH:11][C:10]3[C:5](=[CH:6][CH:7]=[C:8]([CH2:13][CH2:14][CH2:15][CH2:16][N:17]([CH2:21][CH2:22][CH3:23])[CH2:18][CH2:19][CH3:20])[CH:9]=3)[CH:4]=2)[C:46](=[O:48])[C:45]2=[CH:49][CH:50]=[CH:51][CH:52]=[C:44]12

Komponenten

6

Edukt 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 210843912-Hydroxymethyl-6-(4-dipropylaminobutyl)naphthaleneHCID 66777355Diethylazodicarboxylate toluene

Produkt 1

HCID 210843922-Phthalimidomethyl-6-(4-dipropylaminobutyl)naphthaleneAusbeute 75,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The compound (70.0 mg) obtained in Example 124-2 was added with triphenylphosphine (76.1 mg) and phthalimide (36.1 mg), and then dissolved in anhydrous THF (1.0 ml). Subsequently, the solution was added with a 40% diethyl azodicarboxylate/toluene solution (0.132 ml) in an ice bath and stirred at room temperature for 3 hours under a nitrogen atmosphere. After completion of the reaction, the solvent was distilled off and the residue was then purified through silica gel column chromatography (hexane/ethyl acetate), thereby obtaining the subject compound (75.0 mg) as a white solid.

Aufarbeitung

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off
  3. customthe residue was then purified through silica gel column chromatography (hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-d97294e706a744f6a7c3a9a2717cc7f4
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07833991B2

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