(2R,3R,4R,5S)-2-(hydroxymethyl)-1-methylpiperidine-3,4,5-triol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 179 mg of nojirimycin is dissolved in 20 ml of water, followed by adding 1 ml of formalin, adding 100 mg of platinum on carbon catalyst and carrying out a catalytic reduction at ordinary temperature and under atmospheric pressure. The following treatments are carried out in the same manner as in Example 2 to obtain 150 mg (85%) of N-methyl moranoline.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

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.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 179 mg of nojirimycin is dissolved in 20 ml of water, followed by adding 1 ml of formalin, adding about 0.5 ml of Raney nickel catalyst and stirring in a hydrogen stream, at ordinary temperature, under atmospheric pressure, for 3 hours. After completion of the reaction, the catalyst is separated by filtration; the resulting filtrate is passed through a column containing about 100 ml of Dowex 50 W×4 (H); and after washing the column, the resulting adsorbed substances are eluted with 1% aqueous ammonia. The resulting elute is brought to dryness under reduced pressure, and the remaining colorless crystal is recrystallized from ethanol to obtain N-methyl moranoline. After completion of the reaction the catalyst is separated by filtration containing about 100 ml of Dowex 50 W×4 (H) and after washing the column the resulting adsorbed substances are eluted with 1% aqueous ammonia The resulting elute the remaining colorless crystal is recrystallized from ethanol