Allyl bromide → HCID 12140790, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl N-(tert-butoxycarbonyl)-3-(2-propenylamino)propionate (1.12 g, 4.86 mmol) was added 1N solution of lithium bis(trimethylsilyl)amide in tetrahydrofuran (THF) (5.8 mL) and allyl bromide (1.46 mL, 17.0 mmol) successively at −78° C. The mixture was stirred at 0° C. for an hour, then quenched by a saturated aqueous NH4Cl solution and extracted with ethyl acetate. The extract was washed with water and brine, dried over Na2SO4, and evaporated in vacuo. The residue was purified by a silica gel column chromatography eluting with a mixture of ethyl acetate and n-hexane (1:20) to give ethyl N-(tert-butoxycarbonyl)-2-(2-propenyl)-3-(2-propenylamino)propionate (0.7 g, 2.35 mmol, 48.4%) as a colourless oil.

Provenance & Evidence