反应详情

温度

0 °C

To a solution of 6-allyl-3-phenethyl-6-phenyl-[1,3]oxazinan-2-one (100 mg, 0.31 mmol) in dry THF (4 mL) was added dropwise BH3.THF (0.6 mL, 0.62 mmol, 1 M) at 0° C. After 2 h at rt, the reaction mixture was cooled to 0° C., and water (1 mL), aqueous NaOH (1 mL, 3 M) and H2O2 (0.5 mL, 30%) were successively added. The mixture was stirred for 2-3 h at rt, and then diluted with water (8 mL). The pH of the mixture was adjusted to 6-7 with 0.5 N HCl. The layers were separated, and the aqueous phase was extracted with EtOAc (3×6 mL). The combined organic layers were washed with a saturated aqueous NaHCO3 solution (10 mL) and brine (10 mL), dried over Na2SO4, and concentrated in vacuo to give the crude product, which was purified by preparative TLC to afford two isomers of 6-(3-hydroxypropyl)-3-phenethyl-6-phenyl-1,3-oxazinan-2-one.

1. customThe layers were separated
2. extractionthe aqueous phase was extracted with EtOAc (3×6 mL)
3. washThe combined organic layers were washed with a saturated aqueous NaHCO3 solution (10 mL) and brine (10 mL)
4. dry with materialdried over Na2SO4
5. concentrationconcentrated in vacuo
6. customto give the crude product, which
7. customwas purified by preparative TLC