Methanol → [1-(2,6-Dichloropyridin-3-yl)cyclopropyl]methanamine

Participants

Reaction Conditions

Reaction Steps

To a solution of 1.50 g of 1-(2,6-dichloro-pyridin-3-yl)-cyclopropanecarbonitrile in dry toluene was added slowly at −10° C. 14.8 mL of diisobutylaluminium hydride. The reaction mixture was stirred at −10° C. for 30 min. Subsequently, 1.90 g of sodium borohydride and 20 ml of methanol were added sequentially. The speed of addition was such as to maintain the temperature of the reaction mixture below −5° C. The resulting reaction mixture was stirred at −10° C. for 30 min before being quenched by the addition of 35 ml of a aqueous saturated solution of sodium potassium tartrate and extracted with three portions of diethyl ether. The organic phases were combined, washed with brine, dried over sodium sulphate, filtered and concentrated. 1.66 g of crude material was obtained as yellow oil which was purified by flash chromatography on silica gel with dichloromethane/methanol (95:5) as a solvent. Thus, 367 mg of C-[1-(2,6-dichloro-pyridin-3-yl)-cyclopropyl]-methylamine was obtained as a colorless oil. 1H-NMR (CDCl3): 7.63 ppm (d, 1H), 7.23 ppm (d, 1H), 2.85 ppm (s, 2H), 1.46 (m, 1H), 0.93 ppm (m, 2H), 0.83 ppm (m, 2H).

Provenance & Evidence