Tetrabutylammonium Fluoride → HCID 58968741, compound

Participants

Reaction Steps

To a solution of N-(2-(1-methoxycycloheptyl)-5-(trifluoromethyl)benzyl)-N-(3,5-bis(trifluoromethyl)benzyl)-2-(2-(tert-butyldimethylsilyloxy)ethyl)-2H-tetrazol-5-amine (42 mg, 0.056 mmol) in 2-methyltetrahydrofuran (1.5 mL) was added tetrabutylammonium fluoride (0.1 mL; 0.1 mmol; 1.0M in tetrahydrofuran). Reaction was stirred at room temperature for 1.5 hours. The reaction was concentrated in vacuo. The residue was purified by 4 g RediSep column (Teledyne Isco Inc., Lincoln Nebr.) (eluted with 10-40% ethyl acetate in heptane) to give 34 mg (95% yield) of a gum. MS (ES+): Calc: 639.5, Found: 640.5 (M+H). 1H NMR (400 MHz, CDCl3) δ ppm 7.78 (s, 1H), 7.74 (s, 2H), 7.45 (m, 3H), 5.10 (s, 2H), 4.81 (s, 2H), 4.61 (t, J=4.98 Hz, 2H), 4.11 (q, J=6.22, 5.8 Hz 1, 2H), 2.94 (s, 3H), 2.44 (t, J=6.64, 6.22 Hz, 1H), 2.11 (m, 2H), 2.19 (m, 2H), 1.82-1.45(m, 8H).

Provenance & Evidence