Water → Ethyl 4-(3-cyano-2,3,4,5-tetrahydrooxepin-3-yl)piperazine-1-carboxylate

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Reaction Steps

4,5-Dihydrooxepin-3(2H)-one (220 mg, 1.962 mmole) and zinc iodide (31 mg, 0.097 mmole) were combined neat. To this was added TMSCN (0.28 ml, 2.089 mmole) slowly (cooling with cold water bath). After 1 hr a solution of 1-ethoxycarbonylpiperazine (0.32 ml, 2.195 mmole) in MeOH (10 ml) was added then the mixture was heated to reflux. After 16 hr the mixture was cooled to RT and concentrated. Flash column chromatography (25% EtOAc/hexanes) gave the title compound as a clear oil (320 mg, 58%). 1H-NMR (CDCl3, 500 MHz) 6.32 (d, J=6.34 Hz, 1 H), 4.80 (m, 1 H), 4.31 (d, J=12.94 Hz, 1 H), 4.15 (m, 3 H), 3.55 (bs, 4 H), 2.64 (bs, 4 H), 2.30 (bs, 3 H), 2.16 (m, 1 H), 1.27 (t, J=7.08 Hz, 3 H).

Provenance & Evidence