Methanol → HCID 23453188, compound

Participants

Reaction Steps

5.3 g of 2-aminomethyl-2-hydroxymethyl-3,4,5-trihydroxypiperidine dihydrochloride (Example 11) are dissolved in 20 ml of water, and 30 ml of methanol and 8.4 ml of triethylamine are added. 7.8 ml of chloroformic acid hexyl ester, dissolved in 30 ml of ethyl acetate are added dropwise to this solution at 0°-5° C. After stirring the mixture at room temperature for three hours, it is concentrated. The evaporation residue is partitioned in water/ethyl acetate, the phases are separated and the ethyl acetate phase is washed 1× with water. The combined aqueous phases are stirred with 80 g of Amberlite IR A 400, OH- form for 1 hour, the mixture is filtered and the filtrate is concentrated. The evaporation residue is dissolved in a little methanol and the solution is discharged onto a column 120 cm long and 4 cm wide which contains cellulose as the stationary phase and acetone as the mobile phase. The column is washed with acetone. The substance is obtained by elution with 95% pure acetone. After concentrating the eluate, 2.4 g of an almost colourless yellow foam are obtained.

Provenance & Evidence