1-Hydroxybenzotriazole → HCID 56941482, compound

Participants

Reaction Steps

3,5-Difluorobenzoic acid (0.082 g, 0.52 mmol) was added to a stirred solution of 4,5,6,7-tetrahydro-2-(phenoxymethyl)-oxazolo[5,4-c]pyridine (0.10 g, 0.43 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.10 g, 0.52 mmol), 1-hydroxybenzotriazole (0.070 g, 0.52 mmol) and N,N-diisopropylethylamine (0.15 mL, 0.87 mmol) in anhydrous DMF (2.2 mL) under N2. The reaction mixture was stirred at room temperature for 16 hours, diluted with H2O and extracted with AcOEt. The organic layer was separated, extracted with brine, dried (Na2SO4), filtered and the solvent evaporated in vacuo. The crude product was purified by flash column chromatography (silica; 7 N solution of ammonia in MeOH in DCM 0/100 to 5/95). The desired fractions were collected and the solvents evaporated in vacuo to yield 5-(3,5-difluorobenzoyl)-4,5,6,7-tetrahydro-2-(phenoxymethyl)-oxazolo[5,4-c]pyridine (0.086 g, 53% yield) as a colorless oil. C20H16F2N2O3. (mixture of rotamers 65:35) 1H NMR (500 MHz, CDCl3) δ ppm 2.71 (br. s., 1.3 H), 2.79 (br. s., 0.7 H), 3.66 (br. s., 1.3 H), 4.02 (br. s., 0.7 H), 4.50 (br. s., 0.7 H), 4.80 (br. s., 1.3 H), 5.13 (br. s., 2 H), 6.82-6.95 (m, 1 H), 6.95-7.09 (m, 5 H), 7.31 (t, J=7.8 Hz, 2 H).

Provenance & Evidence