Ethyl Bromide → 3-(1-Ethyl-1-hydroxy-propyl)-beta-carboline

HRID 569021Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 569021
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[C:3]([C:14]([OH:16])=O)[N:2]=1.[Mg].[CH2:18](Br)[CH3:19].[Cl-].[NH4+].O1CC[CH2:25][CH2:24]1>C(OCC)C>[CH2:24]([C:14]([C:3]1[N:2]=[CH:1][C:13]2[NH:12][C:11]3[C:6]([C:5]=2[CH:4]=1)=[CH:7][CH:8]=[CH:9][CH:10]=3)([OH:16])[CH2:18][CH3:19])[CH3:25]

Komponenten

7

Edukt 5

HCID 6332Ethyl BromideHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 1732629H-Pyrido(3,4-b)indole-3-carboxylic acidHCID 5462224Magnesium

Produkt 1

HCID 201483963-(1-Ethyl-1-hydroxy-propyl)-beta-carboline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

480 mg of β-carboline-3-carboxylic acid estyl ester are dissolved in 40 ml of tetrahydrofuran and added drop by drop to a Grignard solution consisting of 144 mg of magnesium chips and 660 mg of ethylbromide in 10 ml of diethyl ether. After 2 hours of reflux it is mixed with aqueous ammonium chloride solution and extracted with methylene chloride. After drying, filtering and evaporation, the residue is chromatographed on silica gel with toluene/glacial acetic acid/water=10:10:1 as eluant. 120 mg of 3-(1-ethyl-1-hydroxy-propyl)-β-carboline are obtained as oil.

Aufarbeitung

  1. additionadded drop by drop to a Grignard solution
  2. temperatureAfter 2 hours of reflux it
  3. extractionextracted with methylene chloride
  4. customAfter drying
  5. filtrationfiltering
  6. customevaporation
  7. customthe residue is chromatographed on silica gel with toluene/glacial acetic acid/water=10:10:1 as eluant

Quellen und Nachweise

ORD-Eintrag
ord-4025818dea8b449b85a31db86c7ee7b1
Quelldatensatz
uspto-grants-1988_03
Patentnummer
US04731358

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