Malonate Ion → HCID 34178610, compound

Participants

Reaction Conditions

Reaction Steps

A solution of the malonate (0.92 g, 6.97 mmol) in THF (5 mL) was cooled to 0° C. under N2. Isopropylmagnesium chloride (6.97 mL, 2.0 M) was added and the reaction was stirred for 30 min at 0° C., 30 min at room temperature and 30 min at 40° C. The solution was then cooled to 0° C. and the crude solution of (R)-3-(imidazole-1-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester was added via cannula. A thick precipitate formed. The reaction was warmed to room temperature and stirred under N2 for 12 h. The reaction mixture was cooled to 0° C. and ice-cold 1.0 M H3PO4 (20 mL) was added to the mixture. After 5 min, the reaction was extracted with EtOAc (3×20 mL). The combined organic extracts were washed with sat. NaHCO3 (15 mL) and brine (15 mL), dried over MgSO4 and concentrated to afford crude (R)-3-(2-ethoxycarbonyl-acetyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (0.91 g, crude 69%). The material was used without further purification.

Provenance & Evidence