Ethanol → N-Methyl-1-Deoxynojirimycin

HRID 1759246Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1759246
[CH2:1]([OH:12])[C@H:2]1[NH:7][CH:6](O)[C@H:5]([OH:9])[C@@H:4]([OH:10])[C@@H:3]1[OH:11].[CH2:13](O)C.C=O>O.[Pd]>[CH3:13][N:7]1[C@H:2]([CH2:1][OH:12])[C@@H:3]([OH:11])[C@H:4]([OH:10])[C@@H:5]([OH:9])[CH2:6]1

Komponenten

6

Edukt 3

HCID 702EthanolHCID 712FormaldehydeHCID 65242(3R,4S,5R,6R)-6-(Hydroxymethyl)-2,3,4,5-piperidinetetrol

Produkt 1

HCID 92381N-Methyl-1-DeoxynojirimycinAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

179 mg of nojirimycin is dissolved in 20 ml of a 50% water-containing ethanol, followed by adding 1 ml of formalin, adding 100 mg of palladium on carbon catalyst and carrying out a catalytic reduction at ordinary temperature and under atmospheric pressure. The subsequent treatments are carried out in the same manner as in Example 2 to obtain 144 mg (81%) of N-methyl moranoline.

Quellen und Nachweise

ORD-Eintrag
ord-e6756b2e29234c909cd9d3ae9183869f
Quelldatensatz
uspto-grants-1982_07
Patentnummer
US04339585

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