Trifluoroacetic acid → HCID 45275679, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl N-Boc-4-methylpiperidine-4-carboxylate (130 mg, 0.47 mmol) in CH2Cl2 (8 mL) was added trifluoroacetic acid (0.86 mL, 11 mmol) and the reaction stirred at r.t. for 2 hr before evaporation and aziotrope with toluene (2×25 ml). The crude was dissolved in NMP (4.3 ml) and 3,4,5-trichloropyridine (135 mg, 0.74 mmol) was added followed by triethylamine (0.42 mL, 3.0 mmol) and the mixture was heated in a microwave reactor at 220° C. for 60 min. The mixture was poured into a saturated solution of sodium hydrogen carbonate (50 mL) and extracted with EtOAc (2×100 mL). The combined organic extracts were washed with water (2×50 mL), brine (50 mL), dried (MgSO4) and concentrated under reduced pressure to give a crude pale brown/orange oil (175 mg). The crude product was purified by flash column chromatography on silica gel (cyclohexane, EtOAc, 99:1-88:12, biotage 25+S) to furnish the title compound as a clear colourless oil (85 mg, 56%), LC-MS (ESI, 4 min) Rt 3.36 min, m/z 317 (100%, [M+H]+); m/z (ESI) C14H18N2O2Cl2 requires 316.0745, found [M+H]+ 316.0745.

Provenance & Evidence