Sodium Thiosulfate → HCID 12140789, compound

Participants

Reaction Steps

To a solution of ethyl N-(tert-butoxycarbonyl)-3-(3-hydroxybutylamino)propionate (1.06 g, 3.66 mmol) in dichloromethane (DCM)(15 mL) was added Dess-Martin periodinate (1.17 g, 4.03 mmol). The mixture was stirred for 2 hours, then, a mixture of a saturated aqueous NaHCO3 solution and Na2S2O3 was added. The organic layer was washed with water and brine, dried over Na2SO4, and evaporated in vacuo. The residue was dissolved in THF (10 mL), then a Wittig reagent, which was prepared from methyltriphenylphosphonium bromide (1.57 g, 4.4 nmmol) and 1N-tert-BuOK solution in THF (4.4 mL), in THF (10 mL) was added to the solution at 0° C. The mixture was stirred for an hour at room temperature, then quenched by a saturated aqueous NH4Cl solution, and extracted with ethyl acetate. The organic layer 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 (1:10) to give ethyl N-(tert-butoxycarbonyl)-3-(4-pentenylamino)propionate (487 gm, 1.71 mmol, 46.6%) as a colourless oil.

Provenance & Evidence