Trifluoroacetic acid → 2-methylpropyl[3-fluoro-4-(tetrahydro-2H-thiopyran-4-yl)phenyl]carbamate

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Reaction Steps

A solution of 2-methylpropyl [3-fluoro-4-(tetrahydro-4-hydroxy-2H-thiopyran-4-yl)phenyl]carbamate (See Org. Proc. Res. Dev. 2001, 5, 80-83, 4.00 g, 12.2 mmol) in trifluoroacetic acid (19 mL, 244 mmol) under N2 was treated with triethylsilane (5.85 mL, 36.6 mmol) dropwise, stirred for 1 hr, and then added dropwise to saturated aqueous potassium carbonate (250 mL) with vigorous stirring. The mixture was extracted with diethyl ether (200 mL), and the organic phase was washed with water (2×50 mL) and saline (50 mL), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Trituration and filtration from diethyl ether/hexanes or ethyl acetate/hexanes gave the title compound, 1H NMR (CDCl3, 400 MHz) δ 7.26 (m, 1H), 7.11 (t, 1H), 6.97 (m, 1H), 6.59 (bs, 1H), 3.95 (d, 2H), 2.85 (m, 3H), 2.68 (m, 2H), 2.09 (m, 2H), 1.98 (m, 1H), 1.84 (m, 2H), 0.96 (d, 6H).

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