Formic Acid → 2-(Hydroxymethyl)-1-methyl-3,4,5-piperidinetriol

A mixture of 7 ml of aqueous formalin, 15 ml of formic acid, 1.5 g of 2-hydroxymethyl-3,4,5-trihydroxypiperidine, m.p. 204°-205°, [α]D25 +45° (H2O), is heated under reflux for 20 hours. The reaction mixture is then concentrated to dryness under reduced pressure, the residue is dissolved in water and the insolubles are removed by filtration. The filtrate is passed over ion exchange resin column (Dowex 50 W×4). The column is rinsed with water and the absorved material is eluted with 0.28% aqueous ammonia. The eluate is concentrated to dryness under reduced pressure and the crystalline residue is recrystallized from ethanol to yield 2-hydroxymethyl-3,4,5-trihydroxy-N-methylpiperidine, m.p. 142°-143°, [α]D24 +15.5° (H2O), yield 1.2 g. Treatment with an equimolar amount of p-toluenesulfonic acid gives the corresponding p-toluenesulfonate which, in turn, is recrystallized from methanol. m.p. 198°-199°, [α]D24 +12.2° (methanol).

1. temperatureis heated
2. temperatureunder reflux for 20 hours
3. concentrationThe reaction mixture is then concentrated to dryness under reduced pressure
4. dissolutionthe residue is dissolved in water
5. customthe insolubles are removed by filtration
6. washThe column is rinsed with water
7. washthe absorved material is eluted with 0.28% aqueous ammonia
8. concentrationThe eluate is concentrated to dryness under reduced pressure
9. customthe crystalline residue is recrystallized from ethanol

ORD record

ord-76a1d9a17fc5449385b017cf5c5220bb

Source dataset

uspto-grants-1980_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04182767