Toluene → N-[4-(1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl)-2(R),3(S)-dimethylbutanoyl]-4(R)-isopropyl-2-oxazolidinone

Participants

Reaction Conditions

Reaction Steps

To the imide of Example 7, Step 7, isomer A (200 mg, 0.369 mmol) dissolved in THF (2.0 mL) at -78° C. was added a solution of KHMDS (0.5 mL) in toluene (1.10 mL, 0,660 mmol). The temperature was then increased slowly to -40° C. To the mixture recooled at -78° C. was added MeI (100 mL). The temperature was allowed to wam slowly to -40° and the reaction was quenched by the addition of 25% aqueous solution of NH4OAc. The mixture was extracted with EtOAc, dried over Na2SO4, evaporated in vacuo and purified by flash chromatography (20% EtOAc in hexane) to afford the title product (100 mg).

Provenance & Evidence