Triethylamine → Isopropyl 4-((methylsulfonyloxy)methyl)piperidine-1-carboxylate

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Reaction Steps

A solution of 1-methylethyl 4-(hydroxymethyl)-1-piperidinecarboxylate (prepared as in Example 9, Step 1, 0.5 g, 2.36 mmol) in CH2Cl2 (5 mL) was cooled to 0° C. Et3N (0.5 mL, 3.54 mmol) was added, followed by dropwise addition of methanesulfonyl chloride (0.2 mL, 2.60 mmol). The reaction mixture was allowed to warm up to ambient temperature and stirred for 1 h and diluted with CH2Cl2. The mixture was washed with water, saturated aqueous NaHCO3, brine and dried over Na2SO4, filtered, and the filtrate was concentrated to give 0.71 g of the crude 1-methylethyl 4-{[(methylsulfonyl)oxy]methyl}-1-piperidinecarboxylate as a light brown solid, which was used without further purification. 1H NMR (400 MHz, CDCl3): δ 4.90 (septet, 1H, J=6.2 Hz), 4.25-4.15 (m, 2H), 4.06 (d, 2H, J=6.6 Hz), 3.01 (s, 3H), 2.80-2.65 (m, 2H), 2.00-1.85 (m, 1H), 1.80-1.65 (m, 2H), 1.30-1.15 (m, 8H).

Provenance & Evidence