Sodium borohydride → HCID 58109462, compound

Participants

Reaction Steps

A mixture of 0.0163 g of 4-(3-((S)-1-(4-methoxyphenyl)ethyl)-6-methyl-2-oxo-1,3-oxazinan-6-yl)benzaldehyde isomer 2, obtained as described above, and 0.100 g of NaBH4 in MeOH (3 mL) was stirred at room temperature for 24 h. After the solvent was evaporated, the residue was purified by reversed-phase HPLC (SunFire™ Prep C18 OBD™ 5 μm 19×50 mm column, 10%→90% CH3CN/H2O, 0.1% CF3COOH over 8 min and then 90% CH3CN/H2O, 0.1% CF3COOH over 2 min, flow rate 20 mL/min) to afford (S)-6-(4-(hydroxymethyl)phenyl)-3-((S)-1-(4-methoxyphenyl)ethyl)-6-methyl-1,3-oxazinan-2-one. LC-MS Method 1 tR=1.43 min, m/z 356 (MH+); 1H NMR (400 MHz, CD3OD) δ 7.42-7.25 (m, 4H), 7.14 (d, J=8.8 Hz, 2H), 6.81 (d, J=8.8 Hz, 2H), 5.50 (q, J=7.3 Hz, 1H), 4.53 (s, 2H), 3.69 (s, 3H), 2.70-2.65 (m, 2H), 2.36-2.30 (m, 1H), 1.98-1.87 (m, 1H), 1.50 (s, 3H), 1.19 (d, J=7.3 Hz, 3H).

Provenance & Evidence