Sodium hydride → HCID 58109266, compound

Participants

Reaction Steps

A mixture of crude tert-butyl 3-hydroxy-3-phenylbutyl((S)-1-phenylethyl)carbamate, obtained as described above, 60% NaH in oil (0.320 g) and THF (5 mL) was heated to reflux for 21 h. The reaction was then quenched with H2O (1.5 mL) and diluted with CH2Cl2. The organic layer was dried over Na2SO4. After the solvents were evaporated, the residue was purified by reversed-phase HPLC to afford 6-methyl-6-phenyl-3-((S)-1-phenylethyl)-1,3-oxazinan-2-one. After the solvents were evaporated, the residue was purified by reversed-phase HPLC (Phenomenex® Luna 5μ C18(2) 100 A, 250×21.20 mm, 5 micron, 10%→90% CH3CN/H2O, 0.1% CF3COOH over 13 min and then 90% CH3CN/H2O, 0.1% CF3COOH over 4 min, flow rate 25 mL/min) to afford 6-methyl-6-phenyl-3-((S)-1-phenylethyl)-1,3-oxazinan-2-one as a mixture of diastereomers. LC-MS Method 1 tR=1.71, 1.75 min, m/z=296 (MW); 1H NMR (400 MHz, CD3OD) δ 7.36-7.18 (m), 7.06-7.02 (m), 6.89-6.85 (m), 5.54 (q, J=7.1 Hz), 5.47 (q, J=7.0 Hz), 3.00-2.95 (m), 2.73-2.69 (m), 2.40-2.34 (m), 2.26-2.19 (m), 2.13-2.05 (m), 2.00-1.92 (m), 1.53 (s), 1.52 (s), 1.45 (d, J=7.0 Hz), 1.23 (d, J=7.0 Hz). A fraction containing on the less polar diastereomer was also isolated (Isomer 1). LC-MS Method 1 tR=1.75 min, m/z=296 (MH+); 1H NMR (400 MHz, CD3OD) δ 7.35-7.18 (m, 10H), 5.54 (q, J=7.0 Hz, 1H), 2.72-2.69 (m, 2H), 2.39-2.33 (m, 1H), 1.99-1.92 (m, 1H), 1.52 (s, 3H), 1.23 (d, J=7.0 Hz, 3H).

Provenance & Evidence