Allyl iodide → HCID 20640175, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 15.5 gm of 3-phenylacetyl-4-(S)-benzyl-2-oxazolidinone (52 mmol) in 100 mL of THF at −78° C. in a nitrogen atmosphere was added dropwise 63 mL of a 1M solution of lithium bis(trimethylsilyl)azide (63 mmol). The reaction mixture was warmed to 0° C. over the period of 1 hr and then recooled to −78° C. To the reaction mixture was added 5.3 mL of allyl iodide (57 mmol). The reaction mixture was slowly warmed to room temperature and stirred for 12 hr. The reaction was quenched with saturated NH4Cl solution and the mixture was extracted with ethyl acetate. The combined organic fractions were washed with solutions of saturated NaHCO3 and NaCl, dried over MgSO4, filtered and concentrated. The residue was purified by chromatography (silica, 2:1 hexanes:ethyl acetate) to give the title compound.

Provenance & Evidence