Triethylamine → HCID 86596145, compound

Participants

Reaction Steps

To (1R/S,2R/S,3R/S,6S/R)-3-{[(4-fluorophenyl)sulfanyl]methyl}bicyclo[4.1.0]heptane-2-carboxylic acid (310 mg, 1.12 mmol), PyBOP (640 mg, 1.23 mmol), and aminoacetonitrile hydrochloride (228 mg, 2.46 mmol) was added dry dimethylformamide (10 mL) under an atmosphere of dry nitrogen followed by triethylamine (550 μL, 3.92 mmol) and the reaction mixture was stirred for 4.5 h at room temperature. The reaction mixture was poured into aqueous saturated sodium hydrogen carbonate, extracted with ether, and dried over anhydrous sodium sulfate. The solvent was concentrated in vacuo and the crude product was purified by flash chromatography over silica gel (ethyl acetate/hexanes, 4/6) to yield (1R/S,2R/S,3R/S,6S/R)-N-(cyanomethyl)-3-{[(4-fluorophenyl)sulfanyl]methyl}-bicyclo[4.1.0]heptane-2-carboxamide. 1H NMR (400 MHz, acetone-d6): δ=7.85 (1H, br s), 7.42-7.35 (2H, m), 7.11-7.05 (2H, m), 4.314.19 (2H, m), 2.98 (1H, dd), 2.83 (1H, m), 2.72 (1H, dd), 1.94 (1H, m), 1.85-1.75 (2H, m), 1.54 (1H, m), 1.27-1.16 (2H, m), 0.98 (1H, m), 0.63 (1H, dt). MS [ESI, (M−H)−] m/z=317.0 amu.

Provenance & Evidence