Tetrabutylammonium Fluoride → HCID 67271139, compound

Participants

Reaction Steps

To a solution of (4S,5S)-4-(3,5-difluorobenzyl)-5-((R)-2-benzhydryl-8-(triisopropylsilyloxy)-1,2,3,4-tetrahydroisoquinolin-3-yl)oxazolidin-2-one (Step F (13), 200 mg, 0.3 mmol) in THF (5 mL) was added tetrabutylammonium fluoride (118 mg, 0.45 mmol). The mixture was stirred at rt for 1 h. Solvent was removed and the crude mixture was purified by silica gel Flash Chromatography to give 95 mg of the title compound (60% yield): 1H NMR (CD3OD, 500 MHz) δ 2.51-2.56 (1H, m), 2.68 (1H, d, J=20 Hz), 3.22 (1H, dd, J=5, 20 Hz), 3.35 (1H, m), 3.53 (1H, dd, J=5, 15 Hz), 3.80 (1H, d, J=15 Hz), 4.06-4.12 (1H, m), 4.21 (1H, m), 4.80-4.83 (1H, m), 4.91 (1H, s), 6.57 (1H, d, J=10 Hz), 6.66 (1H, d, J=5 Hz), 6.84-6.88 (3H, m), 6.98-7.01 (1H, m), 7.22 (2H, dd, J=10, Hz), 7.28-7.34 (4H, m), 7.46-7.50 (4H, m). MS (ESI) (M−H)− 525.17.

Provenance & Evidence