Borane;tetrahydrofuran → 3-Aminomethyl-6-(iso-propoxy)methyl-pyridine

HRID 1190974Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1190974
B.C1COCC1.[CH:7]([O:10][CH2:11][C:12]1[N:17]=[CH:16][C:15]([C:18]#[N:19])=[CH:14][CH:13]=1)([CH3:9])[CH3:8]>Cl>[NH2:19][CH2:18][C:15]1[CH:16]=[N:17][C:12]([CH2:11][O:10][CH:7]([CH3:9])[CH3:8])=[CH:13][CH:14]=1

Komponenten

4

Edukt 2

HCID 2723981Borane;tetrahydrofuranHCID 584956066-(Iso-propoxy)methyl-pyridine-3-carbonitrile

Produkt 1

HCID 584955003-Aminomethyl-6-(iso-propoxy)methyl-pyridineAusbeute 46,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Versuchsvorschrift

Add a solution of borane-THF complex (4.5 mL, 4.54 mmol, 1M solution in THF) to neat 6-(iso-propoxy)methyl-pyridine-3-carbonitrile (0.4 g, 2.27 mmol) and stir the mixture for 16 h at reflux. Cool to room temperature and stir for 48 h. Add 2N aqueous HCl (10 mL) until gas evolution stops and then concentrate in vacuo. Dissolve the crude mixture in methanol and filter through a SCX-2 column eluting with methanol followed by 3N ammonia in methanol to obtain the title compound (190 mg, 46%).

Aufarbeitung

  1. temperatureat reflux
  2. stirringstir for 48 h
  3. concentrationconcentrate in vacuo
  4. dissolutionDissolve the crude mixture in methanol
  5. filtrationfilter through a SCX-2 column
  6. washeluting with methanol

Quellen und Nachweise

ORD-Eintrag
ord-cdbb2bbeef9b4678b88ab5310ebb326e
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08680091B2

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