Benzyl allyl(2-methylallyl)carbamate → benzyl 3-methyl-2,5-dihydro-1H-pyrrole-1-carboxylate

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Reaction Steps

A solution of benzyl allyl(2-methylallyl)carbamate (20.2 g, 82 mmol) in dichloromethane (500 mL) was purged with argon for 5 min. Grubbs I catalyst (1.694 g, 2.059 mmol) was added and the resulting purple solution was warmed to a gentle reflux under argon for 24 h. The mixture was concentrated and purified by silica gel chromatography, eluting with 0-20% ethyl acetate in hexanes, to give benzyl 3-methyl-2,5-dihydro-1H-pyrrole-1-carboxylate (16.2 g, 91% yield). 1H NMR (400 MHz, chloroform-d) δ ppm 7.65-7.28 (m, 5H), 5.69-5.27 (m, 2H), 4.30-3.91 (m, 5H), 1.84-1.68 (m, 3H); MS (ES+) m/z: 218.2 (M+H).

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