Borane;tetrahydrofuran → 3-Aminomethyl-6-(tert-butylthio)methyl-pyridine

HRID 1190968Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1190968
[C:1]([S:5][CH2:6][C:7]1[N:12]=[CH:11][C:10]([C:13]#[N:14])=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].B.C1COCC1>C1COCC1>[NH2:14][CH2:13][C:10]1[CH:11]=[N:12][C:7]([CH2:6][S:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:8][CH:9]=1

Komponenten

4

Edukt 2

HCID 2723981Borane;tetrahydrofuranHCID 584955036-(Tert-butylthio)methyl-pyridine-3-carbonitrile

Produkt 1

HCID 584954543-Aminomethyl-6-(tert-butylthio)methyl-pyridineAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Dissolve 6-(tert-butylthio)methyl-pyridine-3-carbonitrile (4.9 g, 23.8 mmol) in anhydrous THF (20 mL) under nitrogen and cool the mixture at 0° C. Add borane-THF complex (71.3 mL, 71.3 mmol, 1M solution in THF). Stir the reaction mixture at room temperature overnight. Pour slowly the reaction mixture into ice-cold 2N aqueous HCl (200 mL) and stir the resulting solution for 4 h. Concentrate in vacuo, take up the resulting solid with a minimum amount of methanol and filter through SCX-2 column eluting with methanol followed by 3N ammonia in methanol to obtain the title compound as a yellow oil (3.8 g, 77%). MS (ES+) m/z: 211 (M+H)+.

Aufarbeitung

  1. stirringstir the resulting solution for 4 h
  2. concentrationConcentrate in vacuo
  3. filtrationfilter through SCX-2 column
  4. washeluting with methanol

Quellen und Nachweise

ORD-Eintrag
ord-328a67a8a12d41dc92592be214d64b13
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08680091B2

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