Tetrabutylammonium Fluoride → HCID 178482461, compound

Participants

Reaction Conditions

Reaction Steps

To a 50 ml THF solution of 1.04 g (2.41 mmol) tert-butyl 1-(3-fluorophenyl)-2-oxo-4-{[(trimethylsilyl)methyl]amino}-1,3,8-triazaspiro[4.5]dec-3-ene-8-carboxylate (prepared in the same manner as Intermediate 5-1 above) was added 3.61 mL (3.61 mmol) of a 1.0M tetrabutylammonium fluoride in THF solution over 5 m and the reaction warmed to 60° C. overnight. The reaction was concentrated to dryness in vacuo and the residue treated with 100 mL CH2Cl2. The organic layer was washed with water (1×25 mL), brine (1×25 mL), dried over Na2SO4, filtered and concentrated to dryness in vacuo to give a crude oil (1.6 g). Purification by flash chromatography (0-7.5% MeOH in CH2Cl2 over 25 m) afforded tert-butyl 1-(3-fluorophenyl)-4-(methylamino)-2-oxo-1,3,8-triazaspiro[4.5]dec-3-ene-8-carboxylate 6-2 as a white solid. 1H NMR (CDCl3, 400 MHz) δ 7.39 (m, 1H), 7.12 (m, 1H), 7.03 (d, J=7.95 Hz, 1H), 6.97 (m, 1H), 5.70 (br s, 1H), 3.54 (m, 2H), 3.11 (d, J=4.76 Hz, 3H), 2.02 (m, 2H), 1.92 (m, 2H), 1.42 (s, 9H). High resolution mass spec (FT/ICR): calc M+H=377.1984. found 377.2010

Provenance & Evidence