[C:1](Cl)(=[O:10])[O:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl.[CH2:13]([NH2:17])/[CH:14]=[CH:15]/[CH3:16].CCN(C(C)C)C(C)C>C(#N)C.[Cl-].[Na+].O>[CH2:13]([NH:17][C:1](=[O:10])[O:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)/[CH:14]=[CH:15]/[CH3:16]Benzyl carbonochloridate (22.8 mL, 167 mmol) was added to a solution of (2E)-but-2-en-1-amine hydrochloride (12.0 g, 112 mmol) and Hunig's base (43.2 g, 330 mmol) in acetonitrile (120 mL) under a nitrogen atmosphere at 0° C. The reaction mixture was stirred under nitrogen at 0° C. for 1 hour and then allowed to warm to ambient temperature. After 3 hours, the reaction mixture was diluted with brine (50 mL) and was extracted with ethyl acetate (3×50 mL). The organic layers were combined, dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford the crude product residue. The crude product residue was purified by silica gel chromatography (ethyl acetate/petroleum ether) to give benzyl (2E)-but-2-en-1-ylcarbamate. MS ESI calc'd. for C12H16NO2 [M+H]+ 206. found 206.
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