Formaldehyde → 3-(2-Ethoxy-carbonyl-allyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Participants

Reaction Steps

Diethyl amine (0.34 mL; 3.3 mmol) was added to a mixture of 2-(1-tert-butoxycarbonyl-pyrrolidin-3-ylmethyl)-malonic acid monoethyl ester (0.69 g, 2.19 mmol) in 36% aqueous solution of formaldehyde (0.27 mL, 3.5 mmol), CH2Cl2 (1.6 mL) and water (1.6 mL) at 0° C. The reaction mixture was stirred at room temperature overnight, poured onto ice-water (500 mL) and extracted with CH2Cl2. The combined organic phases were washed with 5% NaHCO3, dried and concentrated under reduced pressure to yield 3-(2-ethoxy-carbonyl-allyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (0.55 g, 87%) as a colourless oil.

Provenance & Evidence