C([N:8]1[C@@H:13]([CH3:14])[CH2:12][O:11][CH:10]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N+:16]=2[O-])[CH2:9]1)C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[CH3:14][C@@H:13]1[NH:8][CH2:9][CH:10]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[O:11][CH2:12]1To a suspension of 10% palladium-on-carbon (2 g) in ethanol (30 mL) was added a solution of 2-((5S)-4-benzyl-5-methylmorpholin-2-yl)pyridine 1-oxide (3.5 g, 13.06 mmol) in ethanol (10 mL). The mixture was subjected to a hydrogen atmosphere using a balloon filled with hydrogen gas for 2 h. The mixture was filtered through Celite and the filtrate was concentrated under reduced pressure to afford (5S)-5-methyl-2-(pyridin-2-yl)morpholine (0.7 g). MS (ES+) (M+H) 179.0.
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