Acetic Acid → HCID 68953978, compound

Participants

Reaction Steps

To a solution of dimethyl 4-benzyloxy-1-(2-oxopropyl)-1H-pyrazole-3,5-dicarboxylate (80 mg, 0.231 mmol) in anhydrous CH2Cl2 were added methylamine (173 μL, 2.0M in THF), sodium triacetoxyborohydride (98 mg, 0.462 mmol), and AcOH (20 μL, 0.346 mmol). The reaction was stirred at room temperature overnight. Toluene was added to replace the evaporated solvent, and the mixture was heated to 110° C. for 3 h. The solvent was removed in vacuo, and purification was achieved by reverse phase chromatography on a C-18 column using a gradient elution of 95-5% H2O (0.1% TFA)/CH3CN (0.1% TFA). Collection and concentration of the appropriate fractions afforded the title product as a yellow oil. ES MS (M+1)=330.

Provenance & Evidence