Allyl bromide → 3-(2-[3-(2-Methyl-[1,3]dioxolan-2-yl)-propyl]-pent-4-enoyl)-oxazolidin-2-one

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 2-3 (6.0 g, 23.3 mmol) and THF (125 mL) at −78° C. was added LiN(TMS)2 (18.9 mL, 37.8 mmol, 1.0 M in THF) dropwise over 10 minutes. After 20 minutes, allyl bromide was added. After 10 minutes, the reaction was warmed to 0° C. After 4.0 h, the reaction was diluted with EtOAc, washed with sat. NaHCO3, brine, dried (MgSO4) and concentrated. Flash chromatography (silica, 50% EtOAc/hexanes) gave 2-4 as an yellow oil.

Provenance & Evidence