Methyl 6-aminonicotinate → (6-Aminopyridin-3-yl)methanol

Participants

Reaction Steps

To a cold (0° C.) mixture of 6-Aminonicotinic acid methyl ester (0.511 g, 3.36 mmol) and Cerium(III) chloride heptahydrate (1.25 g, 3.36) in dry THF was slowly added lithium borohydride (8.4 mL, 1 M in THF) over a 30 minute period. The mixture was allowed to warm to room temperature overnight then slowly quenched by the addition of ice water (20 mL). After stirring for 1 hr the mixture was filtered through Celite diluted with EtOAc (30 mL) and layers were separated. The aqueous layer was further extracted with EtOAc (1×). The combined EtOAc extracts were washed with brine, dried over MgSO4, evaporated in vacuo and provide a crude semi-solid. The white solid product was triturated with diethyl ether, filtered and dried under reduced pressure.

Provenance & Evidence