Allyl bromide → HCID 85970119, compound

Participants

Reaction Steps

13.06 g of the above prepared (2,2-dimethyl-propionylamino)-acetic acid ethyl ester (69.75 mmol) was dissolved in 350 ml of abs. THF and cooled down to −78°. 146 ml of 1M lithium hexamethyldisilazide in THF (2.1 eq.) were slowly added via dropping funnel. After keeping the yellow suspension for 30 Min. at −78°, 6.491 ml of allyl bromide (1.1 eq.) was added and stirring continued for 15 Min. at the same temperature and for 40 Min. at 0°. Pouring of the homogeneous reaction mixture onto crashed ice/HCl, twofold extraction with AcOEt, twofold washing with water, drying over sodium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, hexane/AcOEt=8/2) afforded 10.50 g of the title compound as colorless solid. In addition, 2.70 g of the di-allylated product (2-allyl-2-(2,2-dimethyl-propionylamino)-pent-4-enoic acid ethyl ester) was obtained from the less polar fractions.

Provenance & Evidence