4-Toluenesulfonyl chloride → 2-(P-Tolylsulfonyl)-6-oxa-2-azaspiro[2.5]octane

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A solution of 4-aminotetrahydro-2H-pyran-4-methanol (16 g, 122 mmol) in dichloromethane (700 mL) was treated with triethylamine (85 mL, 610 mmol), p-toluenesulfonyl chloride (69.8 g, 366 mmol) and DMAP (1490 mg, 12.2 mmol) under nitrogen. After approximately 18 hours at room temperature, the reaction was filtered through a pad of silica gel. The filtrate was concentrated in vacuo then purified by chromatography on silica gel (5-20% EtOAc/hexane) to afford intermediate the title compound (12.5 g) as a white solid.

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