Synthesis
Step 2: Preparation of (4-methylmorpholin-3-yl)methanol
To a solution of morpholin-3-ylmethanol (0.540 g, 4.6 mmol) in methanol (20 mL) was added formaldehyde (1.86 g, 23 mmol, 37% aqueous solution) and palladium/carbon catalyst (0.200 g). The reaction mixture was stirred overnight at room temperature under hydrogen atmosphere (1.0 atm). Upon completion of the reaction, the catalyst was removed by filtration through a diatomaceous earth pad and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent ratio: methanol:dichloromethane=1:15) to afford (4-methylmorpholin-3-yl)methanol (0.130 g, 22% yield) as a yellow oil.
