Tetrabutylammonium Fluoride → HCID 178501185, compound

Participants

Reaction Conditions

Reaction Steps

cis-Methyl 4-((E)-2-(4-fluorobenzoylimino)-6-((triisopropylsilyloxy)methyl)-2,3-dihydro-1H-benzo[d]imidazol-1-yl)cyclohexanecarboxylate (0.61 g, 1.048 mmol) was suspended in 2.1 mL of THF and cooled to 0° C. under nitrogen. To this mixture was added TBAF (1 M in THF) (1.573 mL, 1.573 mmol) dropwise via syringe, and the resulting mixture was stirred for 30 minutes at 0° C. The ice bath was removed, and the mixture was stirred for another 30 minutes at RT. The resulting mixture was diluted with DCM and washed with water. The organic layer was collected, dried over sodium sulfate, and concentrated, and the residue was purified by silica gel chromatography (30-50% EtOAc/Hexanes) to provide the title compound (190 mg, 42.6% yield). MS m/z=426.2 [M+H]. Calc'd for C23H24FN3O4: 425.2. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.63-1.92 (m, 4H) 2.15-2.30 (m, 2H) 2.53-2.74 (m, 2H) 2.78-2.94 (m, 1H) 3.76 (s, 3H) 4.58 (d, J=5.58 Hz, 2H) 4.62-4.82 (m, 1H) 5.24 (t, J=5.58 Hz, 1H) 7.11-7.20 (m, 1H) 7.20-7.33 (m, 2H) 7.35-7.66 (m, 2H) 7.84-8.46 (m, 2H) 12.78 (s, 1H).

Provenance & Evidence