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

Participants

Reaction Conditions

Reaction Steps

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)+.

Provenance & Evidence