Allyl bromide → HCID 69898152, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N-(BOC)-4-oxo-(L)-proline, methyl ester (0.197 g) in 3 mL of THF and 1 mL of DMPU was added 0.28 mL of allyl bromide. The reaction mixture was cooled to −78° C. and 2.0 mL of LiHMDS was dropwise introduced into the reaction. The mixture was stirred at −78° C. for 2 h and then was allowed to warm to rt and stirred under nitrogen overnight. The reaction was quenched with saturated NH4Cl and diluted with water. The mixture was extracted with Et2O (3×). The combined Et2O layers were washed with water, brine and dried over anhydrous Na2SO4. After concentration in vacuo, the crude product was purified by flash column chomatography on silica gel eluted with 5%-10% EtOAc/Hexane to isolate 0.099 g of N-(BOC)-3,3-diallyl-4-oxoproline, methyl ester.

Provenance & Evidence