p-Toluenesulfonic acid monohydrate → (2S,3S)-2-(tert-Butoxycarbonylamino)-3-(benzyloxy)-4,4,4-trifluoro-1-butanol

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Reaction Steps

To a solution of (S)-tert-butyl 4-((R)-1-(benzyloxy)-2,2,2-trifluoroethyl)-2,2-dimethyloxazolidine-3-carboxylate (1.21 g, 3.1 mmol) in methanol (100 mL) was added p-toluenesulfonic acid monohydrate (90 mg, 0.47 mmol). The mixture was stirred at room temperature for 5 days, then the methanol was removed and the residue was dissolved with EtOAc. The EtOAc solution was washed with saturated aq. Na2CO3 solution, water, brine and dried over Na2SO4. Removal of the solvent gave a residue which was purified by flash chromatography to afford the title compound tert-butyl (2S,3S)-3-(benzyloxy)-4,4,4-trifluoro-1-hydroxybutan-2-ylcarbamate (0.54 g, 90%) and recovered starting material (0.54 g). 1H NMR (400 MHz, CDCl3, □ in ppm) 7.31˜7.39 (m, 5H), 5.21 (d, J=7.6 Hz, 1H), 4.87 (d, J=11.1 Hz, 1H), 4.58 (d, J=11.1 Hz, 1H), 4.13 (m, 1H), 4.00 (d, J=11.7 Hz, 1H), 3.83 (m, 1H), 3.65 (d, J=11.7 Hz, 1H), 1.40 (s, 9H).

Provenance & Evidence