Hydrogen Peroxide → HCID 58109163, compound

Participants

Reaction Steps

To a solution of (R)-6-(3-(tert-butyldimethylsilyloxy)propyl)-6-phenyl-3-((S)-1-(4-vinylphenyl)ethyl)-1,3-oxazinan-2-one (20 mg, 0.042 mmol) in dry THF (10 mL) was added BH3 THF (0.5 ml, 0.5 mmol) dropwise at 0° C. After stirring for 2 h at rt, the mixture was cooled to 0° C., and H2O (0.5 mL), 3 M aqueous NaOH (0.5 mL) and 30% H2O2 (0.5 mL) were added successively added. The mixture was stirred overnight at rt. The mixture was diluted with 1 M HCl, and the pH of the mixture was adjusted to 6-7 with 1 M HCl. The layers were separated, and the aqueous phase was extracted with EtOAc (3×5 mL). The combined organic layer was washed with a saturated aqueous NaHCO3 solution (5 mL) and brine (5 mL), dried over Na2SO4, and concentrated in vacuo to give the crude product, which was purified by TLC and preparative HPLC to afford (R)-3-((S)-1-(4-(2-hydroxyethyl)phenyl)ethyl)-6-(3-hydroxy propyl)-6-phenyl-1,3-oxazinan-2-one (7.02 mg, 20%). LC-MS Method 2 tR=1.757, min, m/z=406.2; 1H NMR (CDCl3): 1.31 (m, 1H), 1.47 (d, 3H), 1.68 (m, 1H), 1.89 (m, 2H), 2.18 (m, 2H), 2.70 (m, 1H), 2.83 (m, 1H), 3.49 (m, 2H), 3.71 (m, 2H), 5.58 (m, 1H), 6.75 (m, 2H), 6.88 (m, 2H), 7.23 (m, 5H).

Provenance & Evidence