Tetrabutylammonium Fluoride → 2-(4-tert-Butylphenyl)-N-[(3,4-difluorophenyl)(1-methyl-1H-1,2,3-triazol-4-yl)methyl]acetamide

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Reaction Steps

To a 10 ml round bottom flask containing a solution of 2-(4-tert-butylphenyl)-N-((3,4-difluorophenyl){1-[(trimethylsilyl)methyl]-1H-1,2,3-triazol-4-yl}-methyl)acetamide (0.062 mg, 0.132 mmol) in 1.0 ml of anhydrous THF at rt was added 1.0N tetrabutylammonium fluoride in THF (0.145 ml, 0.145 mmol). The resulting solution was stirred at room temperature for 1 hour. The reaction mixture was diluted with water and extracted with CH2Cl2. The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuum. Purification by preparative HPLC (20-90% CH3CN/H2O over 30 min, 0.05% added TFA, C18 column) to afford 0.046 g (88%) of the title compound. Purification by super fluid (CO2/MeOH) chiral column yielded first enathiomer (19 mg) (36.2%), and second enathiomer (21 mg) (40%) 1H NMR (CDCl3, 400 MHz) δ 7.359 (m, 2H), 7.307 (s, 1H), 7.183 (m, 2H), 7.009 (m, 3H), 6.769 (d, J=7.32 Hz, 1H), 6.216 (d, J=7.57 Hz, 1H), 4.059 (s, 3H), 3.581 (ABq, J=15.75 Hz, 2H), 1.311 (s, 9H). ES-MS [M+1]+: 399.2.

Provenance & Evidence