N-(tert-Butoxycarbonyl)-1,5-diaminopentane → N-(tert-butoxycarbonyl)-N'-(5-isoquinolyl)-pentamethylenediamine

HRID 10511

Reaktionsgleichung

Reaktionsgleichung von HRID 10511
Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.[C:33]([O:37][C:38](=[O:46])[NH:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][NH2:45])([CH3:36])([CH3:35])[CH3:34].CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1>[C:33]([O:37][C:38]([NH:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][NH:45][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2)=[O:46])([CH3:36])([CH3:35])[CH3:34]

Komponenten

6

Edukt 4

HCID 4352N-(tert-Butoxycarbonyl)-1,5-diaminopentaneHCID 7364875-BromoisoquinolineHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 23676156Sodium t-butoxide

Produkt 1

HCID 21979906N-(tert-butoxycarbonyl)-N'-(5-isoquinolyl)-pentamethylenediamineAusbeute 84,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

Under nitrogen atmosphere, a suspension of 5-bromoisoquinoline (245 mg), tris(dibenzylideneacetone)palladium(0) (56 mg), 2-(di-tert-butylphosphino)biphenyl (69 mg), N-(5-aminopentyl)carbamic acid tert-butyl ester (282 mg, Tokyo Kasei Kogyo) and sodium tert-butoxide (160 mg) in toluene was stirred with heating at 70° C. for 4.5 hours. The reaction mixture was cooled to room temperature and purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1) to obtain the title compound (327 mg).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. custompurified by silica gel column chromatography (n-hexane:ethyl acetate=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-600f4b91275841b0837efb247cf9997c
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094789B2

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