1,8-Diazabicyclo(5.4.0)undec-7-ene → Tert-butyl 4-methylpent-3-enyloxycarbamate

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Reaction Steps

To a solution of 5-bromo-2-methylpent-2-ene (1.33 mL, 10.0 mmol) in CH3CN (25 mL) was added tert-butyl hydroxycarbamate (2.0 g, 15.0 mmol) and DBU (4.5 mL, 30 mmol) at 0° C. and the reaction mixture stirred at r.t. for overnight. Quenched with saturated NH4Cl solution and extracted with brine. Combined organic layers washed with brine and dried over anhydrous Na2SO4, filtered and concentrated to provide yellow oil, which was purified by flash chromatography (50% EtOAc-hexane) to yield tert-butyl 4-methylpent-3-enyloxycarbamate (750 mg, 70%) as a viscous oil. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.40 (s, 9H) 1.54 (s., 3H) 1.61 (s., 3H) 2.21-2.31 (m, 2H) 3.70-3.78 (m, 2H) 5.02-5.10 (m, 1H). MS (ES) [M+H] calculated for C11H22NO3, 216.15; found 216.10.

Provenance & Evidence