Water → (5S)-5-(2-methylpropyl)morpholin-3-one

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Reaction Steps

(S)-2-Chloro-N-[1-(hydroxymethyl)-3-methylbutyl]acetamide, 26.34 g (0.136 mol), is dissolved in 450 ml of tetrahydrofuran, the solution is cooled to 0°-5° C. and 7.8 g (0.195 mol) of 60% sodium hydride in mineral oil dispersion is slowly added. The mixture is allowed to reach room temperature and is stirred for 14 hours. Water, 10 ml, is added, the solvents evaporated in vacuo and the residue suspended in 250 ml of chloroform and washed with 100 ml of water and then a saturated aqueous solution of sodium chloride, 2×200 ml. The chloroform layer is separated, dried over sodium sulfate, and evaporated in vacuo. The residue is purified by chromatography using silica gel and eluting with dichloromethane methanol (95:5) to give (S)-5-(2-methylpropyl)-3-morpholinone, 5.1 g, mp 69°-70°; [α]D25 -13.7° (c 1.11, methanol).

Provenance & Evidence