Boron trifluoride etherate → Indole, 3-(2,3-diaminopropyl)-

HRID 985073Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 985073
B(F)(F)F.CCOCC.[NH2:10][C@H:11]([C:22]([NH2:24])=O)[CH2:12][C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[NH:15][CH:14]=1.CSC.B.[OH-].[Na+]>O.O1CCCC1>[NH2:24][CH2:22][CH:11]([NH2:10])[CH2:12][C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[NH:15][CH:14]=1

Komponenten

7

Edukt 4

HCID 8000Boron trifluoride etherateHCID 14798Sodium HydroxideHCID 439356L-TryptophanamideHCID 12423031(Dimethyl sulfide)trihydroboron

Produkt 1

HCID 40849Indole, 3-(2,3-diaminopropyl)-

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Boron trifluoride etherate (12.3 ml, 0.1 mmole) was added to a tetrahydrofuran (24.4 ml) solution of tryptophan amide (20.3 g, 0.1 mole) at room temperature with stirring. At reflux with constant stirring, borane methylsulfide (32.25 ml, 0.34 mole) was added dropwise. The reaction was heated at reflux with stirring for five hours. A tetrahydroturan:water mixture (26 ml, 1:1) was carefully added dropwise. A sodium hydroxide solution (160 ml, 5N) was added and the mixture heated at reflux with stirring for sixteen hours.

Aufarbeitung

  1. additionwas added dropwise
  2. temperatureThe reaction was heated
  3. temperatureat reflux
  4. stirringwith stirring for five hours
  5. temperaturethe mixture heated
  6. temperatureat reflux
  7. stirringwith stirring for sixteen hours

Quellen und Nachweise

ORD-Eintrag
ord-29bf7e3fd6414a97af8b2b8c2cd8076a
Quelldatensatz
uspto-grants-2005_03
Patentnummer
US06869957B1

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