Methanol → [(S)-2-hydroxy-1-(tetrahydro-pyran-2-ylmethyl)-ethyl]-carbamic acid t-butyl ester

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Reaction Steps

To the a solution of (S)-4-(3,6-dihydro-2H-pyran-2-ylmethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid t-butyl ester (1.15 g, 3.8 mmol) in tetrahydrofuran (2 mL) was added methanol (15 mL) and p-toluene sulfonic acid monohydrate (40 mg). The mixture was stirred at room temperature overnight. Solvents were evaporated and the residue was extracted with ethyl acetate and sodium bicarbonate solution. The organic layer was washed with saturated sodium chloride solution and dried over sodium sulfate. After the evaporation of solvent, an oil was obtained (1.03 g). This oil (1.0 g) was dissolved in ethanol (25 mL) and 5% palladium on carbon (200 mg) was added. The mixture was hydrogenated at 50 psi for 45 min. The resulting mixture was filtered and solvents were evaporated to afford [(S)-2-hydroxy-1-(tetrahydro-pyran-2-ylmethyl)-ethyl]-carbamic acid t-butyl ester (948 mg) as an oil. 1H NMR (300 MHz, CDCl3) δ ppm 1.45 (s, 9H), 1.47-1.74 (m, 6H), 1.74-1.94 (m, 2H), 3.30-3.51 (m, 2H), 3.62 (br. s., 2H), 3.69-3.85 (m, 2H), 3.98 (d, J=10.9 Hz, 1H), 5.25 (br. s., 1H).

Provenance & Evidence