Borane;tetrahydrofuran → [6-(cyclohexyloxy)pyridin-3-yl]methylamine

Participants

Reaction Conditions

Reaction Steps

Dissolve 6-cyclohexyloxy-pyridine-3-carbonitrile (1 g, 5 mmol) in anhydrous THF (7 mL) under nitrogen and cool the mixture at 0° C. Add borane-THF complex (15 mL, 15 mmol, 1M solution in THF) and stir the reaction mixture at room temperature overnight. Pour slowly the reaction mixture into an ice-cold 5N aqueous HCl (50 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 a SCX-2 column eluting with methanol followed by 3N ammonia in methanol to obtain the title compound as a yellow oil (621 mg, 62%). MS (ES+) m/z: 207 (M+H)+.

Provenance & Evidence