Sodium Hydroxide → [2-(Methylamino)pyridin-3-yl]methanol

To a solution of t-butyl 2-(methylamino)nicotinate (45.0 g, 0.216 mol) in dry THF (500 mL) cooled in an ice-bath was added LiAlH4 (9.84 g, 0.259 mol) portionwise over a period of 30 min. After stiring for 1 h at 0° C., the mixture was warmed to room temperature and stirred for 2 h. After cooling in an ice-bath, the excess LiAlH4 was decomposed completely by the careful addition of H2O (10 mL) and 1N NaOH aqueous solution (10 mL). Na2SO4 (100 g) was added and the mixture was filtered through a pad of celite. The filtrate was evaporated under reduced pressure and the resulting residue was purified by column chromatography (400 g of silica gel, eluent: DCM/MeOH=20/1−10/1) to give the desire product which was further purified by recrystallization from DCM-hexane to give 3-hydroxymethyl-2-(N-methylamino)pyridine (m) (22.7 g, 76%); 1H NMR (CDCl3): δ 2.30 (brs, 1H), 3.01 (d, J=4.6 Hz, 3H), 4.58 (s, 2H), 5.40 (brs, 1H), 6.50 (dd, J=5.1 and 7.3 Hz, 1H), 7.21 (dd, J=1.7 and 7.3 Hz, 1H), 8.08 (dd, J=1.7 and 5.1 Hz, 1H).

1. temperatureAfter cooling in an ice-bath
2. filtrationthe mixture was filtered through a pad of celite
3. customThe filtrate was evaporated under reduced pressure
4. customthe resulting residue was purified by column chromatography (400 g of silica gel, eluent: DCM/MeOH=20/1−10/1)
5. customto give the desire product which
6. customwas further purified by recrystallization from DCM-hexane

ORD-Eintrag

ord-808b7577b0d94b38a0308b7113b87761

Quelldatensatz

uspto-grants-2006_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07151182B2