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

Temperature

4 °C

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+].

1. customwas then quenched by the addition of water (0.20 mL) at −20° C
2. additionACN (17 mL) and concentrated aqueous NH3 (1.4 mL) was added to the mixture
3. stirringAfter vigorous stirring for 30 min the suspension
4. concentrationThe combined supernatants were concentrated in vacuo

ORD record

ord-9ee127d55dcf48d8be87dbe47dc3ccd1

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08410134B2