1,1'-Carbonyldiimidazole → 1-[3-[Bis(2-propenyloxy)phosphinyl]-1-Oxopropyl]-L-proline, tert-Butyl Ester

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Reaction Steps

3-[bis(2-propenyloxy)phosphinyl]propionic acid (3.4 g., 0.014 mol.) is dissolved in 75 ml. of acetonitrile and stirred in an ice bath under a drying tube. 1,1'-Carbonyldiimidazole (2.26 g., 0.014 mole) in 25 ml. of acetonitrile is added and the mixture is stirred for 1 hour. L-Proline t-butyl ester (2.38 g., 0.014 mole) is added, the ice bath is removed, and the mixture is stirred overnight. The solution is evaporated in vacuo, the residue dissolved in ethyl acetate and washed with 5% potassium bisulfate, saturated sodium bicarbonate solution and brine, then dried (Na2SO4) and evaporated to a viscous liquid, 1-[3-[bis(2-propenyloxy)phosphinyl)]-1-oxopropyl]-L-proline, tert-butyl ester, yield 4.2 g., 77%.

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