Ethanol → N-Methyldeoxynojirimycin

HRID 1759246Notes

Reaction equation

HRID 1759246 reaction equation
[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

Participants

6

Reactant 3

HCID 702EthanolHCID 712FormaldehydeHCID 6524215218-38-9

Product 1

HCID 92381N-MethyldeoxynojirimycinYield 81%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

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.

Sources & evidence

ORD record
ord-e6756b2e29234c909cd9d3ae9183869f
Source dataset
uspto-grants-1982_07
Patent number
US04339585

Reaction notes

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