Diisopropylethylamine → (S)-tert-Butyl 2-(4-(4-(4-fluorophenyl)-1H-1,2,3-triazol-1-yl)phenyl)morpholine-4-carboxylate

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Reaction Steps

(S)-tert-Butyl 2-(4-azidophenyl)morpholine-4-carboxylate (76 mg, 0.25 mol) was dissolved in diisopropylethylamine (800 mg, 6.24 mmol). 1-Ethinyl-4-fluorobenzene (30 mg, 0.25 mmol) was added, followed by copper(I)-iodide (48 mg, 0.25 mmol). The mixture was stirred for 2 h at room temperature. The green mixture was concentrated on the rotavap, silica gel (0.5 g) was added and after short grinding the mixture was put on a silica gel column for purification. Flash chromatography (5 g silica gel, 10 to 30% ethyl acetate in heptane) yielded a white solid (17 mg, 16%), MS (ISP): 425.2 ([M+H]+).

Provenance & Evidence