Triethylamine → HCID 178472518, compound

Participants

Reaction Steps

A mixture of cis-3-amino-cyclobutanecarboxylic acid ethyl ester hydrochloride (50.7 mg, 0.282 mmol), triethylamine (0.058 mL, 0.423 mmol) and THF (2.5 mL) was stirred at room temperature for 30 minutes. 4-[5-(4-Methylphenyl)-1,2,4-oxadiazol-3-yl]benzaldehyde (74.5 mg, 0.282 mmol) and AcOH (0.50 mL) were added to the reaction mixture and stirred for 30 minutes. Sodium cyanoborohydride (35.4 g, 0.563 mmol) was added to the reaction mixture, stirred for 18 hours, quenched with sat. NaHCO3 and extracted with ethyl acetate. The organic phase was concentrated in vacuo. Purification by flash chromatography (silica, 2:8 EtOAc:hexanes) provided the title compound (43.6 g, 39.8% yield) as a solid.

Provenance & Evidence