Triphenylphosphine → 2-(R)-[2-(N,N-Dimethylamino)ethy]-6-(4-[(4-methoxyphenyl)carbonyloxy]benzyloxy)tetralin

HRID 1242870

Reaktionsgleichung

Reaktionsgleichung von HRID 1242870
N(C(OCC)=O)=NC(OCC)=O.[CH3:13][N:14]([CH2:16][CH2:17][C@@H:18]1[CH2:27][CH2:26][C:25]2[C:20](=[CH:21][CH:22]=[C:23]([OH:28])[CH:24]=2)[CH2:19]1)[CH3:15].[CH3:29][O:30][C:31]1[CH:47]=[CH:46][C:34]([C:35]([O:37][C:38]2[CH:43]=[CH:42][C:41]([CH2:44]O)=[CH:40][CH:39]=2)=[O:36])=[CH:33][CH:32]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH3:13][N:14]([CH2:16][CH2:17][C@@H:18]1[CH2:27][CH2:26][C:25]2[C:20](=[CH:21][CH:22]=[C:23]([O:28][CH2:44][C:41]3[CH:40]=[CH:39][C:38]([O:37][C:35]([C:34]4[CH:33]=[CH:32][C:31]([O:30][CH3:29])=[CH:47][CH:46]=4)=[O:36])=[CH:43][CH:42]=3)[CH:24]=2)[CH2:19]1)[CH3:15]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 99645112-(R)-[2-(N,N-dimethylamino)ethyl]-6-hydroxytetralinHCID 219400704-(Hydroxymethyl)phenyl 4-methoxybenzoate

Produkt 1

HCID 587151182-(R)-[2-(N,N-Dimethylamino)ethy]-6-(4-[(4-methoxyphenyl)carbonyloxy]benzyloxy)tetralinAusbeute 50,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Diethyl azodicarboxylate (40% toluene solution, 0.95 g) was added dropwise to THF solution (6 ml) of 2-(R)-[2-(N,N-dimethylamino)ethyl]-6-hydroxytetralin (300 mg), 4-(hydroxymethyl)phenyl 4-methoxybenzoate (530 mg), and triphenylphosphine (430 mg) under ice-cooling. After stirring for 2 hours at room temperature, the reaction mixture was concentrated. The residue was purified using alumina column chromatography (development solvent; hexane˜hexane:ethyl acetate=10:1), and the titled compound (320 mg) was obtained after recrystallization (ethyl acetate-hexane).

Aufarbeitung

  1. temperaturecooling
  2. concentrationthe reaction mixture was concentrated
  3. customThe residue was purified

Quellen und Nachweise

ORD-Eintrag
ord-eec9e17bd9214b2a983e8fef5d333989
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07115750B1

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