HCID 58109492, compound → HCID 58109208, compound

Participants

Reaction Steps

To a solution of (R)-3-((S)-1-(4-acetylphenyl)ethyl)-6-(3-hydroxypropyl)-6-phenyl-1,3-oxazinan-2-one (40 mg, 0.1 mmol) in THF (10 mL) was added dropwise methylmagnesium bromide (3 M, 1 mL, 1 mmol) at −78° C. under N2. The mixture was stirred at rt for 2 days. The reaction was quenched with water, and the layers were separated. The aqueous layer was extracted with EtOAc (3×). The combined organic layer was washed with brine, dried over Na2SO4 and concentrated to give the crude product, which was purified by preparative HPLC to give (R)-3-((S)-1-(4-(2-hydroxypropan-2-yl)phenyl)ethyl)-6-(3-hydroxypropyl)-6-phenyl-1,3-oxazinan-2-one (5 mg, 13%). 1H NMR (CDCl3): 1.31 (m, 1H), 1.44 (m, 3H), 1.64 (m, 1H), 1.93 (m, 2H), 2.11-2.25 (m, 3H), 2.82 (m, 1H), 3.51 (m, 2H), 5.58 (m, 1H), 6.81 (m, 2H), 7.14 (m, 2H), 7.27 (m, 5H). LC-MS Method 2 tR=1.141, min, m/z=420.

Provenance & Evidence