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A solution of (S)-tert-butyl 3-(aminomethyl)morpholine-4-carboxylate (1.0 g, 4.62 mmol) in MeOH (15 ml) was treated with acetaldehyde (0.204 g, 4.62 mmol). The reaction mixture was stirred at 0° C. for 15 minutes and sodium triacetoxyborohydride (2.450 g, 11.56 mmol) was added all at once. The resulting mixture was stirred for 24 h and the mixture was diluted with DCM (15 ml) and washed with saturated aq. sodium bicarbonate (15 ml). The organic phase dried over sodium sulfate, filtered, and concentrated under pressure to give a residue which was purified by column chromatography (ISCO, 12 g silica gel column, eluting with 0→20% MeOH in DCM) to give (S)-tert-butyl 3-((diethylamino)methyl)morpholine-4-carboxylate (INTERMEDIATE 86, STEP 1).

1. stirringThe resulting mixture was stirred for 24 h
2. washwashed with saturated aq. sodium bicarbonate (15 ml)
3. dry with materialThe organic phase dried over sodium sulfate
4. filtrationfiltered
5. concentrationconcentrated under pressure
6. customto give a residue which
7. customwas purified by column chromatography (ISCO, 12 g silica gel column, eluting with 0→20% MeOH in DCM)