Tetrahydrofuran → HCID 178440768, compound

Participants

Reaction Steps

A solution of 3-cis-amino-cylcobutanecarboxylic acid tert-butyl ester (3.78 g, 19.6 mmol), triethylamine (4.0 mL, 29.4 mmol) and THF (100 mL) was added to a solution of 4-[5-(4-isobutyl-phenyl)-[1,2,4]oxadiazol-3-yl]-benzaldehyde (6.0 g, 19.6 mmol) in acetic acid/THF (1:10, 100 mL) and stirred at room temperature for 1 hour. Sodium triacetoxyborohydride (8.06 g, 39.2 mmol) was added to the reaction mixture, stirred at room temperature for 12 hours, treated with methanol (50.0 mL) and concentrated in vacuo. The resulting residue was taken up in dichloromethane, washed sequentially with brine, saturated NaHCO3 and brine, dried (Na2SO4), filtered and concentrated in vacuo. Purification by flash chromatography (silica, 1:9-1:1 EtOAc:hexanes) provided the title compound (4.0 g, 44% yield) as a solid.

Provenance & Evidence