Aluminate(1-), tetrahydro-, (T-4)- → HCID 67434585, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of (2S,6S)-6-((benzyloxy)methyl)-2-methylmorpholin-3-one (6.12 g, 0.026 mol) in THF (20 mL) under a nitrogen atmosphere at rt was added 1 M tetrahydroaluminate in THF (30 mL, 0.030 mol) dropwise over a 15-min period. The reaction mixture was stirred for 2.5 h after which time it was cooled to 0° C. followed by the slow addition of water (13 mL) and then 1 N aq. NaOH (0.9 mL). The quenched reaction was stirred until the precipitate became granular after which time Celite 545 (10 g) was added followed by filtering over a Celite pad and rinsing three times with DCM (30 mL) and ethyl ether (30 mL). The combined filtrates were concentrated and purified over silica gel (Biotage, eluting with a gradient of 0-5% MeOH in DCM) to provide (2S,6S)-2-((benzyloxy)methyl)-6-methylmorpholine (2.7 g, 0.012 mol, 46.2% yield) after combining the desired fractions, concentration and drying in vacuo.

Provenance & Evidence