Iodine → HCID 58092804, compound

Participants

Reaction Conditions

Reaction Steps

A solution of [but-3-enyl-((S)-1-phenyl-ethyl)-amino]-acetic acid methyl ester [432555-77-6] (20.22 mmol) in THF (10 mL) was slowly added to a solution of lithium diisopropylamide (24.26 mmol) in 1:2 hexanes/THF (30 mL) at −78° C. The reaction mixture was warmed to 0° C., stirred for 1 h and then re-cooled to −78° C. A solution of zinc bromide (50.5 mmol) in Et2O (40 mL) was added and the reaction mixture was then warmed to rt. After stirring for 1 h, the mixture was cooled to 0° C. and iodine (22.24 mmol) was added in portions. The reaction mixture was stirred at 0° C. for 2 h and at rt for another 2 h, diluted with Et2O and then successively washed with a saturated solution of Na2S2O3 and a saturated solution of NH4Cl. The aqueous layers were each back-extracted with Et2O. The combined organic phases were dried (Na2SO4), filtered and concentrated. The residue was purified by silica gel column chromatography to afford the title compound as a red oil. HPLC: tR=3.46 min (method G); ESI-MS: [M+H]+ 374.

Provenance & Evidence