Hexane → tert-Butyl (2R)-2-ethenylpyrrolidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

A flask containing a suspension of methyltriphenylphosphonium bromide (24.04 g, 67.3. mmol) and THF (375 mL) is stirred under nitrogen at −78° C. To this was added a 2.5 M solution of nBuLi in hexane (26.92 mL, 67.3 mmol) over 1 h. A solution of 2-(R)-Formyl-pyrrolidine-1-carboxylic acid tert-butyl ester (6.70 g, 33.65 mmol) in THF (30 mL) is added over 10 minutes and the reaction is warmed to RT. The reaction is quenched with H20 (180 mL) and the mixture concentrated. The residue is extracted with EtOAc (3×150 mL) and the combined extracts are dried over MgSO4 and concentrated. Purification by flash chromatography 20% EtOAc/Hexanes yields the title compound as a yellow oil (5.2 g, 26.4 mmol). 1H NMR (CDCl3, 300 MHz) 5.81-5.63(m, 1H), 5.03(d, 2H), 4.40-4.15(m, 1H), 3.45-3.25(m, 2H), 2.05-1.90(m, 1H), 1.89-1.75(m, 2H), 1.74-1.61(m, 1H), 1.43(s, 9H).

Provenance & Evidence