HCID 58109155, compound → HCID 58109324, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-((S)-6-(4-fluorophenyl)-3-((S)-1-(4-fluorophenyl)ethyl)-2-oxo-1,3-oxazinan-6-yl)acetaldehyde (500 mg, 1.40 mmol) in anhydrous THF (100 mL) was added CH3MgBr (5 mL, 3 mol/L) at −78° C. under nitrogen. The formed mixture was stirred for 3 h at −78° C. The reaction was quenched by water. The organic phase was separated and concentrated to give the crude product, which was purified by TLC and chiral preparative HPLC to afford (6S)-6-(4-fluorophenyl)-3-((S)-1-(4-fluorophenyl)ethyl)-6-(2-hydroxypropyl)-1,3-oxazinan-2-one (19 mg, 4%). LC-MS Method 2 tR=1.92 min, m/z=398; 1H NMR: (400 MHz, CDCl3): δ=1.02 (d, 3H), 1.48 (d, 3H), 1.84 (m, 4H), 2.01 (m, 1H), 2.14 (m, 1H), 2.29 (m, 1H), 2.84 (m, 1H), 3.83 (m, 1H), 5.54 (q, 1H), 6.74 (m, 2H), 6.82 (m, 2H), 6.99 (m, 2H), 7.21 (m, 1H).

Provenance & Evidence