Hexamethylenetetramine → Ethyl (+/-)-4-(4-methoxycarbonyl-1,3-oxazol-2-yl)-3-phenylbutanoate

Participants

Reaction Steps

To a suspension of CuBr2 (1.17 g, 5.26 mmole) in degassed (3×vacuum/N2) CH2Cl2 (6 mL) was added hexamethylenetetramine (737 mg, 5.26 mmole) then DBU (0.78 mL, 5.26 mmole). After 5 min, a solution of ethyl (±)-4-(4-methoxycarbonyl-1,3-oxazolin-2-yl)-3-phenylbutanoate (420 mg, 1.32 mmole) in CH2Cl2 (2 mL) was added dropwise. After 6 hr, the mixture was filtered through a pad of silica gel (EtOAc) and the filtrate was concentrated under reduced pressure. The residue was chromatographed on silica gel (50% EtOAc/hexanes) to give the title compound (267 mg, 64%) as a white solid: MS (ES) m/e 318 (M+H)+.

Provenance & Evidence