Methanamine, N-methoxy-, hydrochloride (1:1) → 4,4,N-Trimethoxy-N-methylbutyramide

Temperatur

-10 °C

To a solution of methyl 4,4-dimethoxy-butyrate(4.99 g, 30.8 mmol) and N,O-dimethylhydroxylamine HCl(4.65 g, 47.68 mmol) in 60 mL of THF at −20° C., is added isopropylmagnesiumchloride(46 mL, 92.28 mmol, 2.0M in THF) maintaining the temperature below −20° C. After stirring at −10° C. for 30 min, the reaction mixture is quenched with 50 mL of water and extracted with 3×80 mL of EtOAc. The combined organic layers is dried over Na2SO4 and filtered through a short silica gel pluge. The solution is concentrated to give 4,4,N-Trimethoxy-N-methyl-butyramide(5.9 g, 99%) as pale liquid. M/Z=191.0

1. temperaturemaintaining the temperature below −20° C
2. customthe reaction mixture is quenched with 50 mL of water
3. extractionextracted with 3×80 mL of EtOAc
4. dry with materialThe combined organic layers is dried over Na2SO4
5. filtrationfiltered through a short silica gel pluge
6. concentrationThe solution is concentrated

ORD-Eintrag

ord-2b6194763bc54e6c963c0d78501603e1

Quelldatensatz

uspto-grants-2008_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07419975B2