Diethyl Malonate → 2-(Cis-4-tert-butoxycarbonylamino-cyclopent-2-enylmethyl)-malonic acid diethyl ester

Participants

Reaction Conditions

Reaction Steps

Diethyl malonate (1.29 mL, 8.5 mmol) was added to a mixture of NaH (60%, 0.34 g; 8.5 mmol) in DMF (10 mL). After stirring at room temperature for 15 min a solution of cis-(4-bromomethyl-cyclopent-2-enyl)-carbamic acid tert-butyl ester (1.95 g, 7.1 mmol) in DMF (12 mL) was added, and the reaction mixture was stirred at 60° C. for 19 h. EtOAc was added and the organic phase was extracted with water and brine, dried and concentrated under reduced pressure to give 2.44 g of the crude product. Purification by flash chromatography (CH2Cl2/EtOAc: 1/0→68/32) afforded of 2-(cis-4-tert-butoxycarbonylamino-cyclopent-2-enylmethyl)-malonic acid diethyl ester (1.47 g, 58%).

Provenance & Evidence