(S)-(+)-5,5-Dimethyl-4-phenyl-2-oxazolidinone → (S)-5,5-dimethyl-3-(1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yl)-4-phenyloxazolidin-2-one

Participants

Reaction Steps

The title compound was prepared as described in General Scheme A substituting (S)-5,5-dimethyl-4-phenyloxazolidin-2-one (commercially available from Sigma-Aldrich, Milwaukee, Wis.) and 6-bromo-3,4-dihydroisoquinolin-1(2H)-one (commercially available from Astatech Inc., Bristol, Pa.). The final reaction mixture was filtered through Celite® brand filter aid with MeOH and DCM, concentrated, and purified (ISCO: 5 g cartridge, 12 g column, 0 to 35 to 100%, 90/10 DCM-MeOH in DCM). Fractions with product were repurified (ISCO: 5 g cartridge, 12 g column, 0 to 100% EtOAc-heptanes) giving (S)-5,5-dimethyl-3-(1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yl)-4-phenyloxazolidin-2-one (79.7 mg, 0.237 mmol, 53.6% yield). 1H NMR (400 MHz, DMSO-d6) δ 7.76-7.80 (m, 1H), 7.70 (d, J=8.51 Hz, 1H), 7.53-7.56 (m, 1H), 7.36 (m, 6H), 5.49 (s, 1H), 3.30 (s, 2H), 2.73-2.88 (m, 2H), 1.62 (s, 3H), 0.90 (s, 3H). m/z (ESI) 337.2 (M+H)+.

Provenance & Evidence