Toluene → 1-(6-Bromo-pyridin-2-yl)-2-methoxymethoxy-1-methoxymethoxymethyl-ethylamine

Temperature

100 °C

To a suspension of 2-(6-bromo-pyridin-2-yl)-3-methoxymethoxy-2-methoxymethoxymethyl-propionic acid (18.0 g) in toluene (150 ml)diphenyl phosphoryl azide (4.08 g, 148.27 mmol) and triethylamine (14.97 g [20.6 ml], 148.27 mmol) were added at rt and stirred at 100° C. for 15 h. Reaction mixture was cooled to rt and concentrated under reduced pressure. The residue obtained was dissolved in THF (600 ml) and 20% NaOH solution was added at rt and stirred for 1 h. Solvent was removed under reduced pressure and the product formed was extracted with ethyl acetate. Organic layer was washed with brine, followed by dried over MgSO4. The organic portion was concentrated under reduced pressure and column chromatographic purification of the crude product using 35% ethyl acetate in hexane furnished title compound as a brown liquid. Yield=15.0 g (88% [2 steps]). TLC (70% ethyl acetate in hexane) Rf=0.51; LCMS: RtH7=0.28, [M+1]=335.0 and 337.0.

1. additionwere added at rt
2. customReaction mixture
3. temperaturewas cooled to rt
4. concentrationconcentrated under reduced pressure
5. customThe residue obtained
6. stirringstirred for 1 h
7. customSolvent was removed under reduced pressure
8. customthe product formed
9. extractionwas extracted with ethyl acetate
10. washOrganic layer was washed with brine
11. dry with materialby dried over MgSO4
12. concentrationThe organic portion was concentrated under reduced pressure and column chromatographic purification of the crude product

ORD record

ord-ec442df059c64201a14f9fdb9fb9ea62

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08865712B2