Sodium Methoxide → methyl (4S)-4-{[(tert-butoxy)carbonyl]amino}cyclopent-1-ene-1-carboxylate

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Reaction Steps

Sodium methoxide (8.23 ml of a 25% wt solution in methanol, 0.05 mol eq) was added dropwise to a stirred solution of (−)-N-Boc 2-azabicyclo[2.2.1]hept-5-en-3-one (150 g, 0.72 mol) in methanol (750 ml) at 0° C. After 30 minutes, the reaction was warmed to room temperature. After 60 h, the reaction was quenched with acetic acid and concentrated to dryness. The residue was redissolved in dichloromethane (700 ml) and washed with water (300 ml), saturated sodium hydrogen carbonate (300 ml) and brine (300 ml). The combined aqueous washings were then back extracted with dichloromethane (300 ml), the organic extracts combined and dried over magnesium sulfate. Filtration and concentration under reduced pressure gave a white solid which was recrystallized from ethyl acetate/heptane to give the title compound as white crystals (130 g, 75%)

Provenance & Evidence