Tetrabutylammonium Fluoride → HCID 59596305, compound

Participants

Reaction Steps

To {3-(3-bromo-phenyl)-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-3H-isoindol-1-yl}-carbamic acid tert-butyl ester (Scheme #6, R) (1.07 g, 1.80 mmol) in tetrahydrofuran (20 mL) was added 1.0 M tetrabutylammonium fluoride in tetrahydrofuran (1.98 mL, 1.98 mmol). After 10 minutes the reaction was quenched with water (50 mL) and extracted twice with ethyl acetate. The organic layer was washed with aqueous saturated sodium chloride, dried over magnesium sulfate and the solvent removed under reduced pressure to give a yellow oil. This was chromatographed on 20 g silica gel eluting with 40% ethyl acetate/hexanes and the combined purified fractions removed of solvent under reduced pressure to give the title compound as a yellow solid (906 mg, quantitative yield). 1H NMR (300 MHz, DMSO-d6/TFA-d) δ 8.64 (d, J=7.7 Hz, 1 H), 7.89 (t, J=7.7 Hz, 1 H), 7.74 (t, J=7.5 Hz, 2 H), 7.61-7.57 (m, 2 H), 7.33 (dd, J=4.7, 1.2 Hz, 2 H), 7.14 (dd, J=6.8, 1.9 Hz, 2 H), 6.78 (d, J=8.9 Hz, 2 H), 1.62 (s, 9 H); MS (APCI+) m/z 479 [M+1]+; tR=2.23 min.

Provenance & Evidence