Allyl iodide → HCID 20640175, compound

Temperature

0 °C

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.

1. customrecooled to −78° C
2. temperatureThe reaction mixture was slowly warmed to room temperature
3. customThe reaction was quenched with saturated NH4Cl solution
4. extractionthe mixture was extracted with ethyl acetate
5. washThe combined organic fractions were washed with solutions of saturated NaHCO3 and NaCl
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated
9. customThe residue was purified by chromatography (silica, 2:1 hexanes:ethyl acetate)

ORD record

ord-0a61bc0286b249b7b42d5526baf032bf

Source dataset

uspto-grants-2001_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06194458B1