Acetonitrile → (6S)-6-(3,5-dimethylphenyl)-1,3-oxazinan-2-one

Participants

Reaction Steps

A stirred solution of (4S)-4-(3,5-dimethylphenyl)-4-hydroxybutanamide (Step B; 204 mg; 0.99 mmol) and iodobenzene diacetate (317 mg; 0.99 mmol) in acetonitrile (8 mL) was heated at 40° C. for 16 h. The reaction was concentrated in vacuo and the residue purified by flash silica gel chromatography (0-100% EtOAc/hexanes gradient) to afford (6S)-6-(3,5-dimethylphenyl)-1,3-oxazinan-2-one as a white solid. LCMS=206.3 (M+1)+. 1H NMR (CDCl3, 500 MHz): δ 7.01 (s, 2H), 7.00 (s, 1H), 5.73 (s, 1H), 5.30 (dd, J=9.8, 2.8 Hz, 1H), 3.50 (dt, J=11, 4.8 Hz, 1H), 3.43-3.38 (m, 1H), 2.35 (s, 6H), 2.26-2.21 (m, 1H), 2.14-2.06 (m, 1H).

Provenance & Evidence