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

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).

1. customSolvents were evaporated
2. extractionthe residue was extracted with ethyl acetate and sodium bicarbonate solution
3. washThe organic layer was washed with saturated sodium chloride solution
4. dry with materialdried over sodium sulfate
5. customAfter the evaporation of solvent
6. customan oil was obtained (1.03 g)
7. waitThe mixture was hydrogenated at 50 psi for 45 min
8. filtrationThe resulting mixture was filtered
9. customsolvents were evaporated

ORD 기록

ord-87d368f0f5984016b80d5b434f9756c4

출처 데이터셋

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07741327B2