Water → HCID 14804578, compound

Participants

Reaction Steps

0.52 g (7.9 mMol) KCN and 0.54 g (7.9 mMol) methylamine hydrochloride are added with stirring at 20° C. to 1.1 g (7.7 mMol) of (2R,3R,5E)-2-hydroxy-3-methyl-5-hepten-1-aldehyde dissolved in 50 ml methanol. After addition of 7.5 ml water the reaction mixture is stirred for a further two hours at room temperature and then concentrated to 1/2 volume on a rotary evaporator at a water-bath temperature of maximally 40° C. The obtained solution is shaken with 300 ml methylene chloride and 200 ml water and the separated organic phase is shaken with a further 100 ml water. The aqueous phases are extracted one after the other using 2×100 ml methylene chloride, the methylene chloride fractions are combined with the first organic extract, and the whole is dried over sodium sulfate, filtered through a G3 -frit and evaporated to yield the title compound as a diastereomeric mixture. This is used directly without further purification.

Provenance & Evidence