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

HRID 380673Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 380673
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 8028TetrahydrofuranLösungsmittel2×

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 tetrahydrofuran: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-f2e1d16ee6fe45898b2aa50aebae811c
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06303610B1

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