Tetrahydrofuran → Benzyl 3-(1,1-dimethylprop-2-en-1-yl)-3-hydroxypyrrolidine-1-carboxylate

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Reaction Steps

To a suspension of benzyl 3-oxopyrrolidine-1-carboxylate (4.50 g, 0.0205 mol), 4-bromo-2-methyl-2-butene (4.75 mL, 0.0412 mol) in 25.0 mL saturated ammonium chloride and tetrahydrofuran (4.75 mL, 0.0586 mol), at room temperature, was added zinc (2.70 g, 0.0412 mol). As soon as stirring was started, gas and heat were evolved. After 30 to 45 min, the resulting light grey mixture was filtered through celite. The filtrate was extracted with EtOAc. The organic layers were combined, washed with brine, dried and evaporated to dryness. The residue was purified on silica gel, eluting with 0 to 40% EtOAc in hexanes, to provide the desired product (5.22 g, 87.89%). LCMS (M+H) 290.2.

Provenance & Evidence