3-(Morpholinosulfonyl)pyridine → 4-(Piperidine-3-sulfonyl)morpholine

참여 물질

반응 단계

4-(Pyridine-3-sulfonyl)-morpholine (25 mmol, 5.7 g) was shaken with platinum (IV) oxide (500 mg) in ethanol (50 mL) at 60° C. under hydrogen at 50 psi for 16 h. Reduction was incomplete so the catalyst was removed by filtration, the solvent evaporated under vacuum and the residue dissolved in a mixture of water (50 mL) and acetic acid (10 mL) with warming. Platinum (IV) oxide (1 g) was added and hydrogenation at 50 psi was continued for a further 70 h at 60° C. The catalyst was removed by filtration and the solvent was evaporated under vacuum to give an orange gum which was redissolved in water and the solution (pH 4-5) was extracted with dichloromethane (×3). The aqueous layer was evaporated to a small volume under vacuum, made strongly basic by the addition of 4 M sodium hydroxide solution, xylenes were added and the solvents were removed under vacuum. The residue was agitated with dichloromethane and anhydrous sodium sulfate, the solids removed by flitration through Celite® and the filtrate evaporated under vacuum to give 4-(piperidine-3-sulfonyl)-morpholine as a waxy orange solid (1.3 g, 22%).

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