(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal → Glucamine

Glucose (0.55 mol; 100 g) was dissolved in 500 ml of H2O, and 40 ml of an 80% hydrazinium hydrate solution (1 mol) were added. The mixture was stirred slowly for 14 h and filled into a high pressure autoclave. Freshly activated Raney nickel (20 g) was added and the mixture was hydrogenated for 3 h at 50° C. while stirring with about 1000 r.p.m. The autoclave was depressurized and the product-catalyst mixture was filtered. The blue filtrate was treated with diacetyldioxime (2,3-butanedionedioxime) to remove the dissolved nickel. The product was concentrated to a clear yellowish syrup and was crystallized in the refrigerator. The white crystals were filtered off and washed with MeOH. If necessary the product was purified using the oxalate method of J. W. Long, G. N. Bollenbach in "Methods of Carbohydrate Chemistry" ed. by R. L. Whistler and M. L. Wolfrom, Academic Press N.Y. 1963, Vol. 2, P. 79). Yield: 80 g ( 80%), m.p.: 127° C.

1. additionfilled into a high pressure autoclave
2. waitthe mixture was hydrogenated for 3 h at 50° C.
3. stirringwhile stirring with about 1000
4. filtrationthe product-catalyst mixture was filtered
5. additionThe blue filtrate was treated with diacetyldioxime (2,3-butanedionedioxime)
6. customto remove the dissolved nickel
7. concentrationThe product was concentrated to a clear yellowish syrup
8. customwas crystallized in the refrigerator
9. filtrationThe white crystals were filtered off
10. washwashed with MeOH
11. customIf necessary the product was purified

ORD-Eintrag

ord-096108ae682b41f1ac6340a44df2ce62

Quelldatensatz

uspto-grants-1996_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05480790