Tetrabutylammonium Fluoride → HCID 57828216, compound

Participants

Reaction Steps

Tetrabutylammoniumfluoride (1.0 M in THF, 1.1 mL) was added to a solution of benzyl 4-[4-(tert-butyldimethylsilyloxy)naphthalen-1-yl]butylcarbamate (19, 500 mg, 1.1 mmole) in THF (5 ml) at room temperature. The reaction mixture was stirred for 2 h. The reaction mixture was concentrated to dryness. The residue was purified by column chromatography (silica gel, 3:1 hexanes/EtOAc) to afford carbamate 20 (230 mg, 61%) as a white solid: 1H NMR (300 MHz, CDCl3) δ 8.25-8.21 (m, 1H), 7.91 (dd, J=6.6, 1.8 Hz, 1H), 7.52-7.43 (m, 2H), 7.35-7.27 (m, 5H), 7.05 (d, J=7.5 Hz, 1H), 6.72 (d, J=7.5 Hz, 1H), 5.10 (s, 2H), 4.75 (br s, 1H), 3.23 (q, J=6.6 Hz, 2H), 2.95 (t, J=7.2 Hz, 2H), 1.76-1.56 (m, 4H).

Provenance & Evidence