Triethylamine → HCID 15870474, compound

Participants

Reaction Steps

To a flask containing N-[[4,5-dihydro-3-[4-[1,2,3,6-tetrahydropyridinyl]-phenyl]-5-isoxazolyl]methyl]acetamide (185 mg, 0.62 mmol) in methylene chloride (20 mL) and triethylamine (0.17 mL, 1.24 mmol) is added acetoxyacetyl chloride (0.09 mL, 0.81 mmol) at 0° C. under an inert atmosphere. The reaction is warmed to ambient temperature, stirred for 2 hours and concentrated in vacuo. The residue is dissolved in methanol (15 mL) and potassium carbonate (260 mg, 1.88 mmol) is added. The reaction is stirred fifteen hours, concentrated in vacuo, and chromatographed on silica gel (230-400 mesh, 100 mL), eluting with chloroform/methanol (98/2). The appropriate fractions are combined (Rf =0.10, TLC, chloroform/methanol, 95/5) and concentrated in vacuo to give the title compound, mp 115-118° C.

Provenance & Evidence