Diisobutylaluminum hydride → 2-(Aminomethyl)-4-methyl-3-pyridinemethanol

Participants

Reaction Conditions

Reaction Steps

A solution of AlCl3 (0.15 g, 1.1 mmol) in anhydrous THF (1.1 mL) was added dropwise to a stirred solution of 2-cyano-4-methyl-nicotinic acid methyl ester (0.10 g, 0.57 mmol) at −35° C. DIBAL (1.5 M in toluene, 3.0 mL, 4.5 mmol) was then added at −95° C. The reaction mixture was allowed to warm to 4° C. over 5 h and was then quenched by the addition of water (0.20 mL) at −20° C. ACN (17 mL) and concentrated aqueous NH3 (1.4 mL) was added to the mixture. After vigorous stirring for 30 min, the suspension was centrifuged and the precipitate suspended in a solution of ACN (5 mL) and concentrated aqueous NH3 (0.5 mL). After vigorous stirring for 30 min the suspension was centrifuged. The combined supernatants were concentrated in vacuo to give the title compound. MS (m/z): 153.0 [M+H+].

Provenance & Evidence