Hydrochloric Acid → HCID 21252774, compound

Participants

Reaction Conditions

Reaction Steps

2-Sulfonyloxy-ethylamine hydrochlorides can be prepared by converting ethanolamine to its N-CBZ derivative, purifying by column chromatography with purity confirmed by TLC, reaction with one equivalent of the appropriate sulfonyl chloride in methylene chloride at 0° C. followed by dropwise addition of one equivalent of triethylamine, stirring one hour at 0° C. and one hour at room temperature, washing with water, drying over sodium sulfate, and evaporation to dryness to yield a syrup, which is purified by column chromatography or preparative TLC. The purified product is characterized by TLC and mass and NMR analysis. The resulting N-CBZ derivative in dioxane in the presence of one equivalent of concentrated hydrochloric acid and 10% Pd/C catalyst is hydrogenated in Parr shaker apparatus for one hour at 15 psig pressure, and the mixture is filtered. The filtration residue (catalyst and ppt.) is washed with MeOH and filtered. Evaporation of the combined dioxane-methanol filtrate to dryness in vacuo yields the 2-mesyloxyethylamine hydrochloride in sufficient purity and yield for use as described above.

Provenance & Evidence