Boron trifluoride etherate → 3-(1H-Indol-3-yl)propane-1,2-diamine

HRID 985073Notes

Reaction equation

HRID 985073 reaction equation
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

Participants

7

Reactant 4

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

Product 1

HCID 408493-(1H-Indol-3-yl)propane-1,2-diamine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-29bf7e3fd6414a97af8b2b8c2cd8076a
Source dataset
uspto-grants-2005_03
Patent number
US06869957B1

Reaction notes

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