Tetrahydrofuran → (R)-3-((S)-1-(4-bromophenyl)ethyl)-6-(3-hydroxypropyl)-6-phenyl-1,3-oxazinan-2-one

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Reaction Steps

To a solution of (R)-6-allyl-3-((S)-1-(4-bromophenyl)ethyl)-6-phenyl-1,3-oxazinan-2-one (11.37 g, 28.5 mmol) in tetrahydrofuran (250 mL) was added BH3 THF (80 mL, 1 mol/L, 4 mmol) at 0° C. under nitrogen atmosphere. The mixture was stirred for 2 h, quenched by addition of water. NaOH solution (3 mol/L, 16 mL) and H2O2 (45 mL) were added to the above mixture. When reaction was over, the mixture was extracted with EtOAc. The combined organic layer was concentrated to give the crude product, which was purified by column chromatography to give (R)-3-((S)-1-(4-bromophenyl)ethyl)-6-(3-hydroxypropyl)-6-phenyl-1,3-oxazinan-2-one (4.32 g, 36.4%). 1H NMR: (400 MHz, CDCl3): δ1.48 (t, 3H), 1.53 (m, 1H), 1.73 (m, 1H), 1.93-1.98 (m, 2H), 2.17-2.28 (m, 3H), 3.57 (t, 2H), 5.59 (m, 1H), 6.72 (m, 2H), 7.20 (m, 2H), 7.25-7.37 (m, 5H).

Provenance & Evidence