Methyl 5-oxo-L-prolinate → HCID 86760067, compound

Participants

Reaction Conditions

Reaction Steps

In a flask methyl(s)-(+)-2 pyrrolidone-5-carboxylate (1.0 g, 6.99 mmol) was dissolved in 40 mL THF and cooled to −78° C. LHMDS (8.0 mL, 8.0 mmol) 1.0M in THF was added and the reaction stirred at −78° C. for 25 mins. The chlorocarbonyl-diazo-acetic acid tert-butyl ester (1.7 g, 8.39 mmol, J. Org. Chem. 1994, 59, 1418) was then slowly added and the reaction stirred at −78° C. for 1.5 h, quenched at −78° C. with 5% citric acid and let warm to room temperature. Diluted with EtOAc, seperated, extracted 2× with EtOAc, washed with brine, and dried with magnesium sulfate. Concentrated under vacuum and purified by flash chromatography (10–30% EtOAc/hexanes) to give the product as a viscous yellow oil (1.1 g, 65%). 1HNMR (300 MHz, CDCl3) δ 1.51 (s, 9H) 2.1(m, 1H) 2.2–2.8 (m, 3H) 3.79 (s, 3H) 4.74 (dd, 1H, J 4.0 8.8).

Provenance & Evidence