tert-Butyl 4'-(bromomethyl)biphenyl-2-carboxylate → 4'-(Aminomethyl)-biphenyl-2-carboxylic acid 1,1-dimethylethyl ester

HRID 1655563Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1655563
[NH:1]1[CH:5]=N[N:3]=[N:2]1.Br[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:15]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:10][CH:9]=1>[Pd]>[N:1]([CH2:5][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[C:15]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:12][CH:13]=1)=[N+:2]=[N-:3].[NH2:1][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:15]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:10][CH:9]=1

Komponenten

5

Edukt 2

HCID 9906257tert-Butyl 4'-(bromomethyl)biphenyl-2-carboxylateHCID 178418441HCID 178418441, Verbindung

Produkt 2

HCID 99710734'-(Aminomethyl)-biphenyl-2-carboxylic acid 1,1-dimethylethyl esterHCID 19792037HCID 19792037, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23938PalladiumKatalysator

Versuchsvorschrift

Following the procedures described in Example 1A, replacing N-triphenylmethyl-5-[2-(4'-bromomethyl)biphenyl)]tetrazole with t-butyl 4'-bromomethyl-biphenyl-2-carboxylate, prepared as described by D. J. Carini, et al. in European Patent Application Number 324,377, published Jul. 19, 1989, the intermediate t-butyl 4'-azidomethyl-biphenyl-2-carboxylate is prepared. The intermediate azidomethyl compound is then hydrogenated as described in Example 1B, using palladium on carbon catalyst instead of Lindlar catalyst, to give the title compound.

Aufarbeitung

  1. customprepared

Quellen und Nachweise

ORD-Eintrag
ord-674be420fae14e75862503b732b4b9eb
Quelldatensatz
uspto-grants-1993_10
Patentnummer
US05250548

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