Methyl iodide → (S)-tert-Butyl 2-(4-(methoxycarbonyl)phenyl)morpholine-4-carboxylate

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Reaction Steps

(S)-4-(4-(tert-Butoxycarbonyl)morpholin-2-yl)benzoic acid [CAS 1131220-40-0], (500 mg, 1.63 mmol) was dissolved in dimethylformamide (8.6 ml). Potassium carbonate (675 mg, 4.88 mmol) and iodomethane (346 mg, 0.152 ml, 2.44 mmol) were added. The reaction mixture was shaken at room temperature overnight. The solution was diluted with water (25 ml) and extracted with ethyl acetate (2×40 ml). The combined organic layer was dried over MgSO4 and evaporated to give a light yellow oil. The crude material was purified by flash chromatography (silica gel, 25% ethyl acetate in heptane). Isolation of a white solid (427 mg, 82%), MS (ISP): 266.1 (100%, [M-tBu+H]+), 222.1 (40%, [M-BOC+H]+), 322.2 (7%[M+H]+).

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