Sodium Hydroxide → (6-Methoxymethoxymethylpyridin-3-yl)methanol

Temperatur

-80 °C

Compound (2) dissolved in tetrahydrofuran (100 ml) is added dropwise to a suspension of lithium aluminum hydride (9 g, 2.18×10−1 mol) in tetrahydrofuran (200 ml) cooled to −80° C. and maintained under an inert atmosphere. The reaction mixture is stirred at −80° C. for 30 minutes after the end of the addition. H2O (18 ml), 10% NaOH in water (23 ml), THF (200 ml) and then H2O (53 ml) are added. The temperature is then returned to room temperature, followed by addition of ammonium acetate (20 g, 2.6×10−1 mol) to the suspension. After 15 minutes, the reaction mixture is filtered through Celite and the filtrate is concentrated under vacuum. The residue is taken up in dichloromethane, the phases are separated by settling and the organic phase is dried over Na2SO4. After concentration under reduced pressure, the residue is purified by filtration through silica (eluent: 96/4 CH2Cl2/methanol). The product obtained (14.2 g) is used in the following step without further purification.

1. temperaturemaintained under an inert atmosphere
2. additionafter the end of the addition
3. customis then returned to room temperature
4. waitAfter 15 minutes
5. filtrationthe reaction mixture is filtered through Celite
6. concentrationthe filtrate is concentrated under vacuum
7. customthe phases are separated
8. dry with materialthe organic phase is dried over Na2SO4
9. concentrationAfter concentration under reduced pressure
10. filtrationthe residue is purified by filtration through silica (eluent: 96/4 CH2Cl2/methanol)
11. customThe product obtained (14.2 g)
12. customis used in the following step without further purification

ORD-Eintrag

ord-a0be40ec11924d10ac762da29510f354

Quelldatensatz

uspto-grants-2009_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07547700B2