Iodoethane → (4R)-1-Boc-4-ethoxy-L-proline

Participants

Reaction Steps

1.72 g of 60% sodium hydride in oil are added, under a nitrogen atmosphere, to a solution of 5 g of (2S,4R)-1-(tert-butoxycarbonyl)-4-hydroxy-2-pyrrolidinecarboxylic acid in 100 ml of THF, and the mixture is stirred for 45 minutes at RT. 3.27 g of ethyl iodide are then added, the mixture is refluxed for 3 hours and stirred for 18 hours while allowing the temperature to return to RT. The reaction mixture is concentrated under vacuum, the residue is taken up in 5% KHSO4 solution and extracted with EtOAc, the organic phase is dried over Na2SO4 and the solvent is evaporated off under vacuum. 4.5 g of the expected product are obtained in the form of an oil.

Provenance & Evidence