Triethylamine → (S)-tert-butyl 2-((methylsulfonyloxy)methyl)morpholine-4-carboxylate

참여 물질

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Methanesulfonyl chloride (12 mL, 0.15 mol) was added to a solution of (S)-tert-butyl 2-(hydroxymethyl)morpholine-4-carboxylate (28 g, 0.13 mmol) in CH2Cl2 (172 mL) and triethylamine (23.4 mL, 0.17 mol) at 0° C. The resulting mixture was stirred at a temperature of from 0° C. to room temperature over 1.5 hr. The mixture was then diluted with water (35 mL), and the phases were separated. The aqueous layer was extracted with CH2Cl2 (3×20 mL). The combined organic layers were washed with brine, dried over MgSO4, and filtered on a pad of silica gel, which was rinsed with CH2Cl2. The filtrate was concentrated under reduced pressure to the title product (37.7 g, 99%) as an oil. 1H NMR (300 MHz, CDCl3) δ ppm 1.55 (s, 9H), 2.77-2.91 (m, 1H), 2.97-3.09 (m, 1H), 3.14-3.15 (m, 3H), 3.57-3.67 (m, 1H), 3.73-3.81 (m, 1H), 3.85-4.10 (m, 3H), 4.31 (d, J=4.79 Hz, 2H).

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